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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
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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)

DE2552638A1 Cited
DE2652676A1 Cited
DE2751597A1 Cited
DE2751624A1 Cited

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