E. R. Squibb Sons, Inc.

Squibb Corporation

Squibb & Sons, Inc.

Zahler, Robert

Jacobs, Glenn A.

Breuer, Hermann

Denzel, Theodor

Hermann Breuer

Uwe D Treuner

Theodor Denzel

Robert Zahler

William H Koster

Henner Straub

William A Slusarchyk

Peter H Ermann

Glenn A Jacobs

Jakob-Matthias Drossard

Theodore Denzel

Ivo Polacek

Tetsuo Miyadera

Uwe D Truener

Peter Hans Ermann

Uwe Dietmar Treuner

Antibiotic activity is exhibited by .beta.-lactams having an ##STR1## substituent (and analogs thereof) in the 1-position and an acylamino substituent in the 3-position.

2-oxoazetidin-1-yloxy acetic acids and analogs

Antibacterial activity is exhibited by .beta.-lactams having a 3-acylamino substituent and having in the 1-position an activating group of the formula ##STR1## wherein R is

2-oxo-1-(((substituted sulfonyl)amino)-carbonyl)azetidines

Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituted and having an activating group in the 1-position of the formula ##STR1## wherein A.sub.1 is a single bond, ##STR2## and A.sub.2 is a single bond, ##STR3##

2-oxo-1-((Substituted sulfonyl)amino)-carbonyl)azetidines

Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituent and having an activating group in the 1-position of the formula ##STR1## wherein R is ##STR2## A.sub.1 is --NH-- or ##STR3## A.sub.2 is ##STR4## or --CH.dbd.CH--.

2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines

Antibacterial activity is exhibited by 2-azetidinones having a 3-acylamino substituent and having an activating group in the 1-position of the formula ##STR1##

2-oxo-1-[[(substituted sulfonyl)amino]carbonyl]azetidines

.beta.-Lactams having a sulfonic acid salt substituent in the 1-position, an acylamino substituent in the 3-position and an --NR.sub.2 R.sub.3 substituent in the 4-position wherein R.sub.2 and R.sub.3 are the same or different and each is ##STR1## or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are attached are ##STR2## R.sub.4 is alkyl, aryl or arylalkyl; and R.sub.5 and R.sub.6 are the same or different and each is hydrogen, halogen, alkyl, alkoxy, alkylthio, alkoxycarbonyl, carboxyl or a carboxyl salt; have antibacterial activity.

4-amino derivatives of 2-oxo-1-azetidinesulfonic acid salts

Antibacterial activity is exhibited by .beta.-lactams having a 3-acylamino substituent and in the 1-position a substituent having the formula ##STR1## wherein R.sub.5 and R.sub.6 are the same or different and each is hydrogen, alkyl, alkenyl, alkynyl, phenyl, substituted phenyl, cycloalkyl or a 4,5,6 or 7-membered heterocycle, or R.sub.5 and R.sub.6 together with the carbon atom to which they are attached are cycloalkyl or a 4,5,6 or 7-membered heterocycle, or one of R.sub.5 and R.sub.6 is hydrogen and the other is azido, halomethyl, dihalomethyl, trihalomethyl, alkoxycarbonyl, alkenyl, alkynyl, 2-phenylethenyl, 2-phenylethynyl, carboxyl, --CH.sub.2 X.sub.1, --S--X.sub.2, --O--X.sub.2, or ##STR2## R.sub.7 is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, 1-(ethoxycarbonyloxy)ethyl, 1,3-dihydro-3-oxo-1-isobenzofuranyl, ##STR3## wherein R' is hydrogen or alkyl, R' is alkyl or phenyl, R'' is hydrogen, methyl or phenyl, and R.sup.iv is hydrogen or together with R'' is --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.5 --; and

((3-Acylamino-2-oxo-1-azetidinyl)oxy)methyl)phosphinic acids

Antibacterial activity is exhibited by compounds having the formula ##STR1## and salts thereof, wherein R.sub.1 is acyl;

2-oxo-1-(aminocarbonylaminosulfonyl-aminocarbonyl)azetidines

Antibacterial activity is exhibited by 2-azetidinones activated in the 1-position with an --SO.sub.3 H group and having in the 3-position an acylamino group of the formula ##STR1##

3-acylamino-2-oxo-1-azetidinesulfonic acids

Antibacterial activity is exhibited by .beta.-lactams having a ##STR1## substituent in the 1-position and an acylamino substituent in the 3-position wherein Z is oxygen or sulfur, and R is alkyl, alkenyl, alkynyl, substituted alkyl, phenyl, substituted phenyl, a 5,6 or 7-membered heterocycle (R.sub.c), phenylalkyl, (substituted phenyl)alkyl, R.sub.c -alkyl or --NR.sub.a R.sub.b wherein R.sub.a and R.sub.b are the same or different and each is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, phenylalkyl, or (substituted phenyl)alkyl or one of R.sub.a and R.sub.b is hydrogen, alkyl, phenyl, substituted phenyl, phenylalkyl or (substituted phenyl)alkyl and the other is amino, alkanoylamino, arylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkylamino, dialkylamino, phenylamino, (substituted phenyl)amino, hydroxy, cyano, alkoxy, phenyloxy, (substituted phenyl)oxy, phenylalkoxy, (substituted phenyl)alkoxy, R.sub.c, R.sub.c -alkyl, R.sub.c -alkoxy, alkylsulfonyl, alkylmethyleneamino, phenylmethyleneamino or (substituted phenyl)methyleneamino.

Antibacterial activity and .beta.-lactamase inhibitory activity is exhibited by .beta.-lactams having a 3-acylamino substituent and in the 1-position a group having the formula ##STR1## wherein R.sub.5 is hydrogen, methyl or ethyl.

3-Acylamino-2-oxoazetidine-1-(.beta.-oxopropionic acid)

Cephalosporins of the formula ##STR1## wherein R is hydrogen, sodium, potassium or certain ester groups; R.sub.1 is in the .alpha.-configuration and is hydrogen or methoxy; R.sub.2 is hydrogen, ##STR2## X is hydrogen, ##STR3## R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl, ##STR4## --(CH.sub.2).sub.n --N--(lower alkyl).sub.2 ; R.sub.6 is hydrogen, sodium, or potassium; n is an integer from 1 to 4; are disclosed. These compounds are useful as anti-bacterial agents.

Iminothiazolyl ureido cephalosporins

Antibacterial activity is exhibited by .beta.-lactams having an --SO.sub.2 --NH--C--R substituent in the 1-position and an acylamino substituent in the 3-position wherein R is alkyl, phenyl, substituted phenyl, phenylalkyl, (substituted phenyl)alkyl, alkoxy, phenyloxy, (substituted phenyl)oxy, phenylalkoxy, or (substituted phenyl)alkoxy.

2-Oxo-1-[(acylamino)sulfonyl]azetidines

Cephalosporins of the formula ##STR1## wherein R is hydrogen, sodium, potassium or certain ester groups; R.sub.1 is in the .alpha.-configuration and is hydrogen or methoxy; R.sub.2 is hydrogen, ##STR2## R.sub.4 is hydrogen or lower alkyl; R.sub.5 is hydrogen, lower alkyl, ##STR3## or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2 ; R.sub.6 is hydrogen, sodium, or potassium; n is an integer from 1 to 4; are disclosed. These compounds are useful as anti-bacterial agents.

Cephalosporins of the formula ##STR1## wherein R is hydrogen, sodium, potassium, or certain ester groups; R.sub.1 is in the .alpha.-configuration and is hydrogen or methoxy; R.sub.2 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl, furyl, or pyridyl, or 2-amino-4-thiazolyl; R.sub.3 is lower alkyl or substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl, or furyl; R.sub.4 is hydrogen or lower alkyl; and X is hydrogen, ##STR2## --O--lower alkyl, or certain substituted or unsubstituted heterothio groups; are disclosed. These compounds possess useful antibacterial activity.

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Wuppertal, Germany

Hermann Breuer