- 6- and 4-substituted-1-azabicyclo(3.2.0)heptan-3, 7-dione-2-carboxylates
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Disclosed are 6- and 4-substituted-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylic acid esters and salts (I) which are useful in the preparation of 6-, 1- and 2-substituted carbapenem antibiotics. STR1 wherein R5 is a pharmaceutically acceptable ester moiety or a removable protecting group or an alkali or alkaline earth metal cation such as sodium or potassium and wherein R1, R2, Rhu 3 and R4 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl and aralkyl. Another embodiment disclosed is a group of compounds having the formula STR2 where X is a leaving group.
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- 6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids
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Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-em-3-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics; such compounds are prepared by total synthesis. STR1 wherein R1 and R2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl and the spiro substituent formed by the joinder of R1 and R2.
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- Process for the preparation of carbapenem antibiotics
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Disclosed is a process for the synthesis of carbapenem antibiotics I and their pharmaceutically acceptable salts and esters from 1: STR1 wherein: R7, R6, R1, R2 and R8 are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, spirocycloalkyl, cycloalkylalkyl, alkylcycloalkyl, aryl, aralkyl, aralkenyl, aralkynyl, heteroalkyl, heteroaralkyl, heterocyclyl and heterocyclyalkyl.
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- 6- And 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acid
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Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids I of the following structure: STR1 wherein R1, R2, R3 and R4 are, inter alia, independently selected from the group consisting of alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable 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.
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- 6-(1-Hydroxyethyl)-2-(2-aminoethylthio)-1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids
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Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-em-3-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics; such compounds are prepared by total synthesis. STR1 wherein R1 and R2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl and the spiro substituent formed by the joinder of R1 and R2.
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- Mechanistic Aspects of Gas-Phase Photodecarbonylation Reactions of Bicyclohexanones
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The gas-phase photodecarbonylation and photofragmentation reactions of substituted bicyclohexan-3-ones have been studied in detail.Photolysis of these ketones yields 1,3-dienes, vinylcyclopropanes, and 1,4-dienes as detectable products.The possible mechanisms for these reactions are discussed in light of the regiochemical and stereochemical results obtained.In addition, methyl substitution at C-6 and C-2 of these ketones has been shown to have a pronounced effect on both product ratios and overall reaction efficiency.These effects are discussed in terms of stereoelectronic and electronic controls of rates of cyclopropane ring opening of intermediate acylcyclopropylcarbinyl diradicals.
- Mariano, Patrick S.,Bay, Elliott,Watson, Darrell G.,Rose, Timothy,Bracken, Christopher
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p. 1753 - 1762
(2007/10/02)
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