EP0001628A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
3-Substituted-6-substituted-7-oxo-1-azabicyclo (3.2.0)-hept-2-ene-2-carboxylic acid, its preparation and pharmaceutical compositions containing it
Assignee: Merck and Co Inc
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Filing: 1978-10-16
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Granted: —
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Expires: 1998-10-16
Abstract
Abstract Disclosed are 3- and 6-substituted 7-oxo-1- aza-bicyclo [3.2.0] hept-2- ene-2- carboxylic acids having the structure: wherein R 6 , R' and R a are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically aceptable salt, ester and amide 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 Grant Christensen
- 👤 Susan Margaret Schmitt
- 👤 David Bruce Randolph Johnston
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 21:21
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/26; A; A61; A61P; A61P31/00; A61P31/04; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
213 words
A compound having the structure: and the pharmaceutically acceptable salts thereof wherein R is H: pharmaceutically acceptable salt cation; or a pharmaceutically acceptable ester moiety; and R 5 , R 7 and R 8 are independently 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; het oaryl, heteroaralkyl, heterocyclyl and heterocyclylalkyl wherein the substituent or substituents relative to the above-named 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 hetero atom or atoms in the above-named heterocyclic moieties are selected from the group consisting of 1-4 oxygen, nitrogen or sulphur atoms; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; when R 7 /R 6 is hydrogen R 6 /R 7 is not 1-hydroxyethyl; when -SR 8 is -SCH 2 CH 2 NH 2 and R 7 /R 6 is hydrogen, R 6 /R 7 is not ethyl.
Claim 2
Dependent Claim
213 words
A compound having the structure: and the pharmaceutically acceptable salts thereof wherein R is H: pharmaceutically acceptable salt cation; or a pharmaceutically acceptable ester moiety; and R 5 , R 7 and R 8 are independently 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; het oaryl, heteroaralkyl, heterocyclyl and heterocyclylalkyl wherein the substituent or substituents relative to the above-named 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 hetero atom or atoms in the above-named heterocyclic moieties are selected from the group consisting of 1-4 oxygen, nitrogen or sulphur atoms; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; when R 7 /R 6 is hydrogen R 6 /R 7 is not 1-hydroxyethyl; when -SR 8 is -SCH 2 CH 2 NH 2 and R 7 /R 6 is hydrogen, R 6 /R 7 is not ethyl.
Claim 3
Dependent Claim
23 words
A compound according to Claim 1 wherein: R 6 is hydrogen or methyl and R 8 is selected from the group consisting of:
Claim 4
Dependent Claim
7 words
or and R 7 is selected from:
Claim 5
Dependent Claim
7 words
or and R 7 is selected from:
Claim 6
Dependent Claim
9 words
A compound according to Claim 2 having the structure:
Claim 7
Dependent Claim
9 words
A compound according to Claim 2 having the structure:
Claim 8
Dependent Claim
59 words
A process for preparing a compound according to Claim 1'comprising: cyclizing in the presence of base: to form: dehydrohalogenating the resulting intermediate in the presence of base to form: heating the resulting intermediate in the presence of a displacing agent to form: isomerizing the position of the double bond of the resulting intermediate to form: wherein X is halo.
Claim 9
Dependent Claim
25 words
6 . A process for preparing a compound according to Claim 1 comprising treating: with a base capable of isomerizing the double bond to form:
Claim 10
Dependent Claim
29 words
7 . A process for preparing a compound of the formula: comprising reacting: with X S R 8 to yield followed by elimination of HX; wherein X is halo.
Claim 11
Dependent Claim
29 words
7 . A process for preparing a compound of the formula: comprising reacting: with X S R 8 to yield followed by elimination of HX; wherein X is halo.
Claim 12
Dependent Claim
19 words
A process for preparing a compound according to Claim 1 comprising reacting: with XSR 8 wherein X is halo.
Claim 13
Dependent Claim
21 words
An antibiotic pharmaceutical composition comprising a therapeutically effective amount of a compound according to Claim 1 and a pharmaceutical carrier therefor.
References Cited (Backward Citations)
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