Otsuka Kagaku Yakuhin Kabushiki Kaisha

Otsuka Kagaku Kabushiki Kaisha

Taiho Pharmaceutical Company Limited

Otsuka Chemical Co., Ltd.

Otsuke Kagaku Yakuhin Kabushiki Kaisha

Norio Saito

Hideo Tanaka

Michio Sasaoka

Sigeru Torii

Takashi Shiroi

Junzo Nokami

Shigeru Torii

Kenji Uneyama

Junzo Nogami

Shigemitsu Nagao

Akira Tanaka

Takashi Siroi

Yutaka Kameyama

Masatoshi Taniguchi

Yoshihisa Tokumaru

Ryo Kikuchi

Yuzuru Ogata

Kiyotoshi Matsumura

Makoto Akizuki

A process for preparing a penicillanic acid compound of the formula (2) comprising reacting a halogenated penicillanic acid compound of the formula (1), (a) in the presence of a metal bismuth or bismuth compound, (b) with a metal having a lower standard oxidation-reduction potential than bismuth to obtain the compound (2) (X and Y are a hydrogen atom or halogen atom, provided that X and Y are not hydrogen atoms at the same time, n is an integer of 0 to 2, R is carboxylic acid protecting group) (n and R are same as above).

Process for producing penicillanic acid compound

Disclosed is a method of producing a 3-exomethylenecepham of the formula ##STR1## wherein R.sup.1 is amino or substituted amino and R.sup.2 is a carboxy-protecting group comprising reacting a cephem of the formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above and X is halogen with lead metal while maintaining the pH of the reaction system at about 0.1 to 8. The cephem (I) may be reacted with a catalytic amount of lead metal or a lead compound in the presence of a metal having a greater ionization tendency than lead.

Method for production of 3-exomethylenecepham derivatives

This invention provides azetidinone derivatives represented by the formula ##STR1## and processes for preparing the same. The azetidinone derivatives are used as the intermediates for producing cephalosporin compounds useful as antibiotic agents.

Process for the preparation of cephem derivatives

An azetidinone derivative represented by the formula (I) ##STR1## wherein R.sup.1 is substituted or unsubstituted phenyl or substituted or unsubstituted phenoxy, R.sup.2 is hydrogen, optionally substituted hydrocarbon residue or aminoprotecting group selected from acyl, silyl, sulfonyl and phosphonyl derived from organic or inorganic acid, ##STR2## (wherein R.sup.3 is hydrogen or lower alkyl), X.sup.1 and X.sup.2 are the same or different and are halogen, hydroxyl, alkoxy, acyloxy, SR.sup.4 (wherein R.sup.4 is straight chain or branched chain lower alkyl substituted or unsubstituted, substituted or unsubstituted phenyl or substituted or unsubstituted heterocyclic group), amino or hydrogen, one of X.sup.1 and X.sup.2 being hydrogen when the other is not, and R.sup.5 is substituted or unsubstituted phenyl or substituted or unsubstituted heterocyclic group, and a process for preparing the same.

Azetidinone disulfide derivatives and a process for preparing the same

An azetidinone derivative represented by the formula (I) ##STR1## wherein R.sup.1 is substituted or unsubstituted phenyl or substituted or unsubstituted phenoxy, R.sup.2 is hydrogen, optionally substituted hydrocarbon residue or amino-protecting group selected from acyl, silyl, sulfonyl and phosphonyl derived from organic or inorganic acid, ##STR2## is &gt;C.dbd.O or&gt;C.dbd.N--OR.sup.3 (wherein R.sup.3 is hydrogen or lower alkyl), X.sup.1 and X.sup.2 are the same or different and are halogen, hydroxyl, alkoxy, acyloxy, SR.sup.4 (wherein R.sup.4 is straight chain or branched chain lower alkyl substituted or unsubstituted, substituted or unsubstituted phenyl or substituted or unsubstituted heterocyclic group), amino or hydrogen, one of X.sup.1 and X.sup.2 being hydrogen when the other is not, and R.sup.5 is substituted or unsubstituted phenyl or substituted or unsubstituted heterocyclic group, and a process for preparing the same.

Azetidinone disulfides and a ring opening process for preparing the same

A process for preparing an azetidinone derivative represented by the formula (I) ##STR1## wherein R.sup.1 represents an aryl group, arylmethyl group or aryloxymethyl group, R.sup.2 represents hydrogen atom or a carboxyl-protecting group and R.sup.3 represents an alkyl group or aryl group, the process comprising reacting an azetidinone derivative represented by the formula (II) ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above with a chlorinating agent.

Halogenation process for preparing

Azetidinone derivatives and process for the preparation of the same

4-thio azetidinone intermediates and process for the preparation of the

Process for preparing cephalosporin compounds

Bicyclic azetidinone intermediates

Process for preparing azetidinone derivatives

2-substituted cephem derivatives and process for preparing the same

This invention provides thiazolinoazetidinone derivatives represented by the formula ##STR1## and processes for preparing the same. The thiazolinoazetidinone derivatives are used as the intermediates for producing cephalosporin compounds useful as antibiotic agents.

Thiazolinoazetidinone derivatives and process for the preparation of the

A process for preparing an azetidinone derivative represented by the formula (1) ##STR1## wherein R.sup.1 represents a substituted or unsubstituted aryl group, a substituted or unsubstituted phenylmethyl group or a substituted or unsubstituted phenoxymethyl group, R.sup.2 represents a hydrogen atom or a group for protecting carboxylic acid and Ar represents a substituted or unsubstituted phenyl group, the process comprising reacting a thiazolineazetidinone derivative represented by the formula (2) ##STR2## wherein R.sup.1 and R.sup.2 are as defined above with a sulfonyl bromide represented by the formula (3)

This invention relates to novel thiazolineazetidinone-type compounds represented by the formula ##STR1## wherein R represents a hydrogen atom, alkyl group, alkyl group replaced with halogen atoms, methyl group replaced with substituted or unsubstituted phenyl groups, methyl replaced with halogen atoms, or trialkylsilyl group and Z represents O or Cl.sub.2.

Thiazolineazetidinone-type compounds

Growing community of inventors

Tokushima, Japan

Norio Saito