Otsuka Kagaku Kabushiki Kaisha

Otsuka Kagaku Yakuhin Kabushiki Kaisha

Taiho Pharmaceutical Company Limited

Otsuke Kagaku Yakuhin Kabushiki Kaisha

Michio Sasaoka

Hideo Tanaka

Sigeru Torii

Takashi Shiroi

Yutaka Kameyama

Norio Saito

Junzo Nokami

Masatoshi Taniguchi

Shigeru Torii

Daisuke Suzuki

Ryo Kikuchi

Junzo Nogami

Shigemitsu Nagao

Kenji Uneyama

Isao Wada

Kiyotoshi Matsumura

Ichiro Kawahara

Seiryu Uto

Mitsuo Akada

Yoshihisa Tokumaru

Akira Tanaka

Yasuhisa Amano

Delsoo Suh

Takashi Siroi

Fumio Toda

Motoaki Tanaka

Hiroki Kourai

Akihiro Shimabayashi

Akira Nakai

Yoshihisa Tomotaki

Yuzuru Ogata

Yoshio Yabuhara

Tsuneyuki Sato

Hiroshi Hama

Syozo Hayase

Kenji Kase

Hitoshi Tanaka

Akihiro Murakami

Kouichi Sorajo

Shiro Yamashita

Akira Suzuki

Kenji Kaze

Kouichi Tanaka

Nori Saito

Todatoshi Ota, Deceased

Kouji Mori

The present invention provides a process for preparing an exo-methylenepenam compound represented by the general formula (5) characterized in that a &bgr;-lactam halide compound represented by the general formula (2) is subjected to an electroreduction process to obtain the exo-methylenepenam compound.

Process for preparing beta lactam compound

A process for preparing an allenyl .beta.-lactam compound represented by the formula (4), characterized by reacting the hydroxyl group of a .beta.-lactam compound represented by the formula (1) with a reactive functional group derivative of sulfonic acid represented by the formula (2) to convert the compound of the formula (1) to a .beta.-lactam compound represented by the formula (3), thereafter reacting the resulting .beta.-lactam compound with a basic anion exchange resin of the type having a tertiary organic base fixed to the resin and isolating the resulting allenyl .beta.-lactam compound of the formula (4) from the reaction mixture ##STR1##

Process for preparing .beta.-lactam derivatives

A process for preparing a 2-isocephem derivative characterized in that a thioacetic acid derivative which itself is basic or a mixture of a base and a thioacetic acid derivative is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-isocephem derivative represented by the general formula (2), and a process for preparing a 2-oxaisocephem derivative characterized in that a base is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-oxaisocephem derivative represented by the general formula (3) ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.1 and R.sup.2, when taken together, form a cyclic amino protecting group, R.sup.3 is a hydrogen atom or carboxylic acid protecting group, W is a leaving group, and X and Y are the same or different and are each a halogen atom.

Process for preparing 2-isocephem derivatives

The present invention provides a process for preparing an exo-methylenepenam compound represented by the general formula (5) characterized in that a .beta.-lactam halide compound represented by the general formula (2) is reduced with a metal having a standard oxidation-reduction potential of up to -0.3 (V/SCE) in an amount of at least one mole per mole of the halide compound and with a metal compound having a higher standard oxidation-reduction potential than the metal in an amount of 0.0001 to 10 moles per mole of the halide compound, or is subjected to an electroreduction process to obtain the exo-methylenepenam compound. ##STR1##

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Tokushima, Japan

Michio Sasaoka