Abstract: Novel antibiotics of the formula: ##STR1## and its salts, esters and amides wherein R is acyl;B is H, OMe, Me or SR wherein R is lower alkyl or aryl;A.sup.1 is hydrogen, hydroxy, or an organic group; and,X is a divalent radical selected from --O--, --CH.sub.2 --, or --NY-- where Y is hydrogen or lower alkyl of from 1 to 6 carbon atoms such as methyl, ethyl, i-propyl, n-butyl, n-pentyl, n-hexyl and the like, formyl or benzyl.This invention is directed to novel antibiotics, novel intermediates useful in their preparation, and processes for preparing the novel antibiotics. The novel antibiotics are effective against gram-negative bacteria including Proteus vulgaris, E. coli and Salmonella schottmulleri, and gram-positive bacteria including Staphylococcus aureus and Bacillus subtilis and are useful in combatting bacterial infections in animals or humans in addition to various industrial applications.

Abstract: Disclosed are 6-amido-3-substituted-amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxyli c acids (I): ##STR1## wherein R.sup.1 is hydrogen or acyl; and R' and R" are independently selected from the group consisting of: hydrogen, substituted and unsubstituted: alkyl and aralkyl, or together form a substituted or unsubstituted cyclic group. Such compounds and 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 is a process for chemically cleaving the acyl group from N-acyl-6-substituted-2-[2-aminoethylthio]-1-carbadethiapen-2-em-3-carboxyl ic acids which proceeds via an imino chloride intermediate. The acylated substrate and the deacylated product are antibiotics.

Abstract: Disclosed is a process for the hydrolytically cleaving O-sulfo thienamycins: ##STR1## wherein R is H or acetyl and M is H, an alkali or alkaline earth metal cation or an organo cationic species such as pyridinium; and wherein the dotted line indicates saturated and unsaturated species.

Abstract: Disclosed is a process for preparing 7-(1-hydroxethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and its pharmaceutically acceptable salts and esters (I) by total synthesis starting with L-aspartic acid and proceeding via intermediates II and IIa (4-iodomethylazetidin-2-one): ##STR1##

Abstract: Novel antibiotics of the formula: ##STR1## and its salts, esters and amides wherein R is acyl; B is H, OCH.sub.3, CH.sub.3 or SR" wherein R" is lower alkyl; A is hydrogen, hydroxy, or an organic group; and, Y is a radical of the formula PO(OH).sub.2 ; PO(OH)(OR") wherein R" is loweralkyl; SO.sub.2 (OH); or SO.sub.2 NH.sub.2.The products are prepared by a multi-step process starting with an .alpha.-aminophosphonoacetate and terminating in the acylation of the 7-amino compound, and, if desired, removing the ester blocking group. The products are useful antibiotics.

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.

Abstract: A novel total synthesis process is provided, yielding cephalosporin or penicillin compounds. The process uses as starting material a glycine ester, which first is reacted to yield a dihydrothiazine, and subsequently condensed with azidoacetyl chloride to form the cepham nucleus, then dehydrated to yield the desired 3-unsaturation. Subsequent reduction and acylation steps are analogous to known chemistry. The end products are antibacterial agents.

Abstract: Cephalosporin antibiotics of the formula: ##STR1## are produced by cycloaddition of a glycine derivative of the formula ##STR2## with a thiazine derivative of the formula ##STR3##

Abstract: Cephalosporin compounds having a loweralkoxy or loweralkylthio substituent in the 6-position are prepared by a multi-step total synthesis route using as starting material a glycine ester, which first is reacted to yield a dihydrothiazine, and subsequently condensed with azidoacetyl chloride to form the cepham nucleus, then dehydrated to yield the desired 3-unsaturation. Subsequent reduction and acylation steps are analogous to known chemistry, and yield the novel 6-loweralkoxy- or loweralkylthio-7-amino intermediates and the antibacterially active 6-loweralkoxy or loweralkylthio-7-acylamido end products.

Abstract: Novel cephalosporin compounds having a 3'-.alpha.-methyl, a 3-aryl or 3-heterocycle substituent are prepared by total synthesis. The novel cephalosporin compounds are active against gram-negative and gram-positive microorganisms.

Abstract: Novel antibiotics of the formula: ##STR1## and its salts, esters and amides wherein R is acyl; B is H, OCH.sub.3, CH.sub.3 or SR" wherein R" is lower alkyl; A is hydrogen, hydroxy, or an organic group; and, Y is a radical of the formula PO(OH).sub.2 ; PO(OH) (OR") wherein R" is loweralkyl; SO.sub.2 (OH); or SO.sub.2 NH.sub.2.The products are prepared by a multi-step process starting with an .alpha.-aminophosphonoacetate and terminating in the acylation of the 7-amino compound, and, if desired, removing the ester blocking group. The products are useful antibiotics.

Abstract: Novel 7-azido-3-cephem compounds are prepared via .alpha.-amino-phosphonoacetate esters. The cephem compounds are intermediates for the preparation of novel and known useful antibiotic cephalosporins.

Abstract: Novel cephalosporin compounds having a 3'-.alpha.-methyl, a 3-aryl or 3-heterocycle substituent are prepared by total synthesis. The novel cephalosporin compounds are active against gram-negative and gram-positive microorganisms.