E. R. Squibb Sons, Inc.

Squibb & Sons, Inc.

Breuer, Hermann

Denzel, Theodor

Theodor Denzel

Hans Hoehn

Hermann Breuer

Uwe D Treuner

Christopher M Cimarusti

William A Slusarchyk

Richard H Mueller

Janak Singh

Ernst Schulze

Hans Joachim Schneider

Peter Schierling

Disclosed herein are processes for preparing a compound of the formula ##STR1## in which a novel compound of the formula ##STR2## is reacted with a beta lactam of the formula ##STR3## by treatment with a base, wherein the symbols are as defined in the specification.

Process and intermediates for beta-lactams having

.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 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 .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.

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

A compound of the formula ##STR1## wherein R is hydrogen, alkali metal, ##STR2## R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen or methyl;

Imidazole derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins

New 4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin-5(8H)on e and new derivatives thereof have the general formula ##STR1## The compounds are useful as anti-inflammatory agents and central nervous system depressants.

4H-Pyrazolo[4',3':5,6]pyri

A compound of the formula ##STR1## wherein R is hydrogen, alkali metal, ##STR2## or ##STR3## R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen or methyl;

Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino]

New derivatives of 8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine have the general formula ##STR1## The compounds are useful as anti-inflammatory agents and central nervous system depressants.

8H-Pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine

The new amino derivatives of pyrido[2,3-d]pyridazine carboxylic esters and acids have the general formula ##STR1## They are useful as analgesic, anti-inflammatory agents and central nervous system depressants. In addition, this type of compound increases the intracellular concentration of adenosine-3',5'-cyclic monophosphate.

Amino derivatives of pyrido(2,3-d)pyridazine carboxylic acids and esters

New derivatives of 8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]-pyrido[3,4-e]pyrimidine have the general formula ##STR1## The compounds are useful as anti-inflammatory agents and central nervous system depressants.

New 4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)one and new derivatives thereof have the general formula ##STR1## The compounds are useful as anti-inflammatory agents and central nervous system depressants.

4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)one and

New 4H-pyrazolo[1,5-a]pyrazolo[4',4':5,6]pyrido[3,4-e]pyrimidin-5(8H)one and new derivatives thereof have the general formula ##STR1## The compounds are useful as anti-inflammatory agents and central nervous system depressants.

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Wuppertal, Germany

Theodor Denzel