US 5,693,792 AGranted

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

AssigneeOtsuga Kagaku Kabushiki Kaisha

InventorsShigeru Torii, Hideo Tanaka, Mitio Sasaoka, Takashi Shiroi, Yutaka Kameyama

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Abstract

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.

Claims1

Dependent claims

A .beta.-lactam compound of the formula ##STR16## wherein R.sup.1 represents a hydrogen atom, a halogen atom, an amino group or a protected amino group;

R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower acyl group, a lower alkyl group, a lower alkyl group substituted by a hydroxyl or protected hydroxyl group, a hydroxyl group or a protected hydroxyl group;
R.sup.1 and R.sup.2 taken together represent .dbd.O;
R.sup.3 represents a hydrogen atom or a carboxyl-protecting group;
R.sup.4 represents an aryl group optionally having at least one substituent selected from the group consisting of halogen, hydroxy, nitro, cyano, aryl, lower alkyl, amino, mono(lower)alkylamino, di(lower)alkylamino, mercapto, R.sup.8 S--, formyloxy, R.sup.8 COO--, formyl, R.sup.8 CO--, R.sup.8 O--, carboxy and R.sup.8 OCO--;
wherein R.sup.8 is a lower alkyl group or an aryl group;
and R.sup.5 represents a vinyl group.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/515,166Filed 15 Aug 1995 · division
Priority: JP 4-3031018 Feb 1992
Granted: 2 Dec 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 205/09
With one oxygen atom directly attached in position 2, e.g. beta-lactams: with a sulfur atom directly attached in position 4
C07D 205/095
With a sulfur atom directly attached in position 4: and with a nitrogen atom directly attached in position 3
C07D 501/00
Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a
Y02P 20/55
Improvements relating to the production of bulk chemicals: design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups