Sankyo Company, Limited

Yuji Iwano

Koichi Hirai

Akira Yoshida

Takahide Nishi

Hiroo Koyama

Kozo Oda

Katsumi Fujimoto

Shuji Takahashi

Akio Torikata

Takeshi Kagasaki

Tetsuo Hiraoka

Yoshiharu Sakaida

Hideyuki Shiozawa

Kentaro Kodama

Akira Ishii

Takuzo Nishimura

Kaneo Ogawa

Tokio Saito

Yukichi Kishida

Yoshiki Matsui

A method for preparing compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; R.sup.4 is hydrogen or an amino-protecting group; and Z is sulfur or oxygen. The process comprises reacting a compound of formula (II): ##STR2## in which R.sup.8, R.sup.9 and R.sup.10 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group, with a compound of formula (III): ##STR3## in which R.sup.11 represents an acyloxy, alkylsulfonyl, arylsulfonyl, alkylsulfinyl or arylsulfinyl group.

Silyl enol ether alkylation process

A process for preparing a compound of formula (I'): ##STR1## comprising reacting a compound of formula (II'): ##STR2## with a compound of formula (III'):

Metal catalyzed displacement process

A compound of the formula ##STR1## in which: R.sup.1' is hydrogen or a carboxy-protecting group;

Carbapenem

Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

Azetidinone compounds useful in the preparation of carbapenem

Two thiomarinol derivatives, which have antibacterial and anti-mycoplasmal properties, are obtainable from microorganisms of the genus Alteromonas and are named 'thiomarinol B' and 'thiomarinol C'. Thiomarinol B can also be prepared by the oxidation of thiomarinol.

Thiomarinol compounds

N-benzhydryl-substituted heterocyclic derivatives, their preparation and

Novel penicillin and cephalosporin derivatives possessing interferon inducibility and represented by the formula ##STR1## wherein Y represents a hydrogen atom, a halogen atom a nitro group, an alkoxy group or an alkyl group; M represents a protective group for a hydroxyl or carboxyl group; Z represents a group ##STR2## or a group ##STR3## in which D is a hydrogen atom, an acyloxy group, a carbamoyloxy group or a substituted or unsubstituted heterocyclic thio group; A represents a cyano group, a carboalkoxy group or a nitro group; and B represents a hydrogen atom, a cyano group, a carboalkoxy group or a nitro group And process for preparing the same.

Penicillin and cephalosporin derivatives and process for preparing the

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Tokyo, Japan

Yuji Iwano