US4347367A
Expired / Lapsed
US
⏱️ 0.0 years remaining
3-Substituted-6-(1'-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid
Assignee: Merck and Co Inc
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Filing: 1980-11-14
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Granted: 1982-08-31
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Expires: 2000-11-14
Abstract
Abstract Disclosed are 3-substituted-6-(1'-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene- 2-carboxylic acids having the structure: <IMAGE> wherein R8 is, inter alia, selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Inventors
- 👤 Burton G. Christensen
- 👤 David B. R. Johnston
- 👤 Susan M. Schmitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:50
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C07C; C07C205/00; C07C205/39; C07C205/42; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D477/26; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
146 words
A compound selected from the group consisting of: ##STR83## wherein: R 4 is hydrogen; R 5 is a removable protecting group or a pharamceutically acceptable ester moiety; and R 8 is selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl, aralkyl, aralkenyl, and aralkynyl wherein the aryl moiety is phenyl and the linear chain has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named R 8 radicals are selected from the group consisting of: amino, mono-, di- and trialkylamino, hydroxyl, alkoxyl, mercapto, alkylthio, phenylthio, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; X is chloro or bromo.
Claim 2
Dependent Claim
146 words
A compound selected from the group consisting of: ##STR83## wherein: R 4 is hydrogen; R 5 is a removable protecting group or a pharamceutically acceptable ester moiety; and R 8 is selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl, aralkyl, aralkenyl, and aralkynyl wherein the aryl moiety is phenyl and the linear chain has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named R 8 radicals are selected from the group consisting of: amino, mono-, di- and trialkylamino, hydroxyl, alkoxyl, mercapto, alkylthio, phenylthio, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; X is chloro or bromo.
Claim 3
Dependent Claim
68 words
A compound having the structure: ##STR84## wherein: R 5 is a removable protecting group or a pharmaceutically acceptable ester moeity; and R 8 is selected from the group consisting of: H, CH 3 , C(CH 3 ) 2 CH 2 NH 2 , ##STR85## CH 2 CH 2 CH 2 NH 2 , CH 2 CH(CH 3 )NH 2 , ##STR86## CH 2 CH 2 NH 2 ##STR87##
Claim 4
Dependent Claim
68 words
A compound having the structure: ##STR84## wherein: R 5 is a removable protecting group or a pharmaceutically acceptable ester moeity; and R 8 is selected from the group consisting of: H, CH 3 , C(CH 3 ) 2 CH 2 NH 2 , ##STR85## CH 2 CH 2 CH 2 NH 2 , CH 2 CH(CH 3 )NH 2 , ##STR86## CH 2 CH 2 NH 2 ##STR87##
References Cited (Backward Citations)
US4234596A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-30 | 1986-03-01 | 1986-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-30 | 1990-03-01 | 1990-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-30 | 1994-03-01 | 1994-08-31 | $7700.00 | Window Closed / Lapsed |