Abstract: Disclosed are 6-, 1- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein: R.sup.1, R.sup.2, R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, 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.

Abstract: Disclosed are substituted N-methylene derivatives of thienamycin having the formula: ##STR1## wherein: (1.) X.dbd.--NR.sup.1 R.sup.2, and Y.dbd.--R'--N.dbd.CRNR.sup.1 R.sup.2, and(2.) X.dbd.R, and Y.dbd.--NR.sup.1 R'N.dbd.CRNR.sup.1 R.sup.2 ; andwherein: R is, inter alia, hydrogen, NH.sub.2, --NHR.sup.1, --NR.sup.1 R.sup.2, R.sup.1 and R.sup.2 ; R.sup.1 and R.sup.2 are independently selected from: hydrogen, substituted, or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R' is --(CH.sub.2).sub.n.sup.-, n is 1-6, or --(CH.sub.2).sub.m --Q--(CH.sub.2).sub.p.sup.-, m, n.dbd.1-3 and Q is O, S or R' is a carbocyclic or heterocyclic ring. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics.

Abstract: Disclosed are 1-substituted-pen-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 R.sup.1 and R.sup.2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, and spirocycloalkyl.

Abstract: Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids I of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 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.

Abstract: Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-e m-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 R.sup.1 and R.sup.2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl and the spiro substituent formed by the joinder of R.sup.1 and R.sup.2.

Abstract: Disclosed are 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, inter alia, independently selected from the group consisting of hydrogen, 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.

Abstract: Disclosed are 6-, 1- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein: R.sup.1, R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, 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.

Abstract: Disclosed are O-, N- and substituted carboxyl derivatives of the antibiotic thienamycin, which has the following structure: ##STR1## Such derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives, and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.

Abstract: Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-e m-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 R.sup.1 is, inter alia, substituted and unsubstituted alkyl, aryl and aralkyl.

Abstract: Disclosed are 1-substituted-pen-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 R.sup.1 is, inter alia, substituted and unsubstituted alkyl, aryl and aralkyl.

Abstract: Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are, inter alia, independently selected from the group consisting of hydrogen, 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 antibiotics effect is indicated.

Abstract: A process is disclosed for preparing antibiotic 6- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids and their pharmaceutically acceptable salts and esters (I) ##STR1## wherein: R.sup.1 and R.sup.2 are selected from hydrogen, alkyl aryl, and aralkyl; and R.sup.3 is hydrogen, --R, --OR, or --SR, wherein R is hydrogen, alkyl, aryl or aralkyl. The process comprises complexing an appropriately substituted .delta.,.omega.-unsaturated amino acid with a transition metal carbonyl complex, followed by oxidatively induced ligand transfer and ring closure: ##STR2## wherein: F.sub.p =.eta..sup.5 --C.sub.5 H.sub.5 Fe(CO).sub.2 and F.sub.p (isobutene.sup..sym. represents a cationic complex between F.sub.p and an olefin such as isobutene, which complex cation is employed in the initial ligand exchange reaction; R.sup.4 is lower alkyl or phenyl; R.sup.5 is a readily removable blocking group or pharmaceutically acceptable ester radical; and R.sup.1, R.sup.2 and R.sup.3 are as defined above.

Abstract: Disclosed are 6-(.alpha.-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid and its 2,3-dihydro analogue, 6-(.alpha.-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. Such compounds and their pharmaceutically acceptable salt, ester, ether and aide derivatives (derivatives involving both the secondary alcohol and the carboxyl group) 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.

Abstract: Disclosed are N-derivatives of thienamycin having structures I and II. ##STR1## wherein: the bifunctional radical may contain additional unsaturation in the ring; and wherein n is an integer selected from 1-6; p is 0, 1 or 2; R.sup.1 is selected from hydrogen, alkyl having 1-6 carbon atoms, and aryl having 6-10 carbon atoms; and Z is imino (.dbd.NH), oxo (.dbd.O), hydrogen, amino, or alkyl having 1-6 carbon atoms. Such compounds and their pharmaceutically acceptable salt and ester 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.

Abstract: The antibiotic .DELTA..sup.3 -thienamycin is disclosed: ##STR1## It is prepared by double bond isomerization of thienamycin. Also disclosed are pharmaceutical compositions comprising .DELTA..sup.3 -thienamycin, and methods of treatment comprising administering .DELTA..sup.3 -thienamycin when an antibiotic effect is indicated.