Otsuka Kagaku Kabushiki Kaisha

Mitio Sasaoka

Hideo Tanaka

Yutaka Kameyama

Takashi Shiroi

Shigeru Torii

Masatoshi Taniguchi

The object of the invention is to provide a .beta.-lactam compound and a 2-substituted methyl-3-cephem compound, both of which are of value as intermediates for the synthesis of cephem antibiotics. The .beta.-lactam compound of the invention may be represented by the general formula ##STR1## wherein R.sup.1 represents a protected amino group, for instance; R.sup.2 represents hydrogen, for instance; R.sup.3 represents hydrogen or a carboxy-protecting group; R.sup.4 represents an aryl group which may be substituted; R.sup.5 represents an alkenyl group which may be substituted, for instance. The 2-substituted methyl-3-cephem compound of the invention may be represented by the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above; R.sup.6 represents an aryl group which may be substituted.

.beta.-lactam and cephem compounds and processes for their production

A penam derivative of the general formula ##STR1## wherein R.sup.1 means hydrogen, halogen, amino or protected amino; R.sup.2 means hydrogen, halogen, lower alkoxy, lower acyl, lower alkyl, hydroxy- or protected hydroxy-substituted lower alkyl, hydroxy or protected hydroxy, or R.sup.1 and R.sup.2 may jointly represent oxo; R.sup.3 means hydrogen or a carboxy-protecting group; R.sup.4 means hydrogen; R.sup.5 means a group of the formula --CH.sub.2 Y where Y means halogen, --N.sub.3, --ONO.sub.2, --OR.sup.6, --OCOR.sup.6, --SCSOR.sup.6, --SCSN(R.sup.6).sub.2, --SR.sup.6, --SO.sub.2 R.sup.6, --NHR.sup.6, --N(R.sup.6).sub.2 or a substituted or unsubstituted nitrogen-containing heterocyclic group having a free valence on nitrogen; R.sup.6 means a lower alkyl, aryl or heterocyclic group which is substituted or unsubstituted; or R.sup.4 and R.sup.5 may jointly represent .dbd.CH.sub.2 ; n means 0, 1 or 2; provided, however, that where R.sup.4 and R.sup.5 jointly represent .dbd.CH.sub.2, n is not equal to 0.

Penam derivatives

The object of the invention is to provide a .beta.-lactam compound and a 2-substituted methyl-3-cephem compound, both of which are of value as intermediates for the synthesis of cephem antibiotics. The .beta.-lactam compound of the invention may be represented by the general formula ##STR1## wherein R.sup.1 represents a protected amino group, for instance; R.sup.2 represents hydrogen for instance; R.sup.3 represents hydrogen or a carboxy-protecting group; R.sup.4 represents an aryl group which may be substituted; R.sup.5 represents an alkenyl group which may be substituted, for instance. The 2-substituted methyl-3-cephem compound of the invention may be represented by the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above; R.sup.6 represents an aryl group which may be substituted.

Growing community of inventors

Tokushima, Japan

Mitio Sasaoka