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Cephalosporin derivatives and use as antimicrobial agents
| Details |
Inventors: Hamberger, Helmut; Fliri, Hans;
Assignee: Sandoz Ltd. (Basel, CH)
Primary Examiner: Coughlin, Jr.; Paul M.
Assistant Examiner:
Attorney, Agent or Firm: Sharkin; Gerald D., Vila; Richard E.
Novel compounds of formula I, ##STR1## in which R.sub.1 is hydrogen, alkyl, phenylalkyl, carbalkoxyalkyl, acyl, carboxyalkyl, alkoxyalkyl, hydroxyalkyl, cyanoalkyl, or carbamoylalkyl, R.sub.2 is hydrogen, pivaloyloxymethyl or the residue of an easily splittable ester grouping, R.sub.3 is a pyrazolyl radical, unsubstituted or mono- or di-substituted by alkyl, phenyl, alkoxy, alkylthio, carboxy, carboxyalkyl, carbamoyl, carbamoylalkyl, alkylsulphonyl, azido, acylamino, hydrazino, acylhydrazino alkylidenehydrazino, phenylidenehydrazino, in which the phenyl nucleus is unsubstituted or substituted by NH.sub.2, lower alkoxy or lower alkyl, furylidenehydrazino, carbalkoxy or a group R.sub.5 R.sub.6 N--, in which R.sub.5 and R.sub.6 are the same or different and are hydrogen or alkyl, provided that the nitrogen atoms and the 4-position of the pyrazole nucleus are either unsubstituted or substituted by alkyl, phenyl, or carbalkoxy, and R.sub.4 is hydrogen, acetoxy, carbamoyloxy or --S--Rh, in which Rh is a heterocyclic radical. |
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DETAILED DESCRIPTION What we claim is: 1.
Compounds of formula I, ##STR40## in which R.
sub.
1 is hydrogen, alkyl, phenylalkyl, carbalkoxyalkyl, C.
sub.
2-5 alkanoyl, alkoxy-carbonyl, carboxyalkyl, alkoxyalkyl, hydroxyalkyl, cyanoalkyl, or carbamoylalkyl, R.
sub.
2 is hydrogen, pivaloyloxymethyl or the residue of an easily splittable ester grouping, R.
sub.
3 is a 3- or 5-pyrazolyl radical, unsubstituted or mono- or di-substituted by alkyl, phenyl, alkoxy, alkylthio, carboxy, carboxyalkyl, carbamoyl, carbamoylalkyl, alkylsulphonyl, azido, C.
sub.
2-5 alkanoylamino, C.
sub.
1-4 alkoxycarbonylamino, benzylcarbonylamino, hydrazino, C.
sub.
2-5 alkanoylhydrazino, alkylidenhydrazino, phenyldenhydrazino, in which the phenyl nucleus is unsubstituted or substituted by NH.
sub.
2, lower alkoxy or lower alkyl, furylidenhydrazino, carbalkoxy or a group R.
sub.
5 R.
sub.
6 N--, in which R.
sub.
5 and R.
sub.
6 are the same or different and are hydrogen or alkyl, provided that the nitrogen atoms and the 4-position of the pyrazole nucleus are either unsubstituted or substituted by alkyl, phenyl, or carbalkoxy, and R.
sub.
4 is hydrogen, acetoxy, carbamoyloxy or --S--Rh, in which Rh is a heterocyclic radical, and pharmaceutically acceptable salts thereof.
2.
Compounds of claim 1, in syn isomeric form or in the form of syn/anti isomeric mixtures in which the syn isomer predominates.
3.
The compound of claim 1, which is 7-{[(pyrazolyl-3)-syn-methoximino]acetylamino}-3-desacetoxy-3-(1-methyltet razolyl-5-thio)cephalosporanic acid sodium salt.
4.
The compound of claim 1, which is 7-{[(pyrazolyl-3)-syn-methoximino]acetylamino}-3-desacetoxy-3-(1-methyltet razolyl-5-thio)cephalosporanic acid pivaloyloxy methyl ester.
5.
The compound of claim 1, which is 7-{[(pyrazolyl-3)-syn-carbethoxymethoximino]acetylamino}-3-desacetoxy-3-(1 -methyl-tetrazolyl-5-thio)cephalosporanic acid.
6.
The compound of claim 1, which is 7-{[(pyrazolyl-3)-syn-carbethoxymethoximino]acetylamino}-3-desacetoxy-3-(1 -methyltetrazolyl-5-thio)cephalosporanic acid pivaloyloxymethyl ester
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