Taiho Pharmaceutical Company Limited

Otsuka Chemical Co., Ltd.

Otsuka Kagaku Kabushiki Kaisha

Other

Akihiro Shimabayashi

Daisuke Suzuki

Yoshihisa Tokumaru

Kiyotoshi Matsumura

Ichiro Kawahara

Shigetoshi Yaguchi

Michio Sasaoka

Masatoshi Taniguchi

Hiroaki Asai

Isao Wada

Hiroshi Akagi

Ichirou Kawahara

Kenji Kaze

An object of the invention is to provide an industrially advantageous process capable of remarkably suppressing the generation of an undesirable by-product cepham compound to thereby efficiently produce a desired 2&#x3b1;-methyl-2&#x3b2;-[(1,2,3-triazol-1-yl)methyl]penam-3&#x3b1;-carboxylic acid ester. In the present invention, a diphenylmethyl 2&#x3b2;-bromomethyl-2&#x3b1;-methylpenam-3&#x3b1;-carboxylate (BMPB) is reacted with 1,2,3-triazole in a halogenated hydrocarbon solvent at &#x2212;5&#xb0; C. or lower. The reaction in a halogenated hydrocarbon solvent at &#x2212;5&#xb0; C. or less can remarkably suppress the generation of an undesirable by-product cepham compound, so that the desired diphenylmethyl 2&#x3b1;-methyl-2&#x3b2;-[(1,2,3-triazol-1-yl)methyl]penam-3&#x3b1;-carboxylate (TMPB) can be efficiently produced.

Process for producing penam compound useful for preparing tazobactam

The present invention provides anhydrous crystals of &#x3b2;-lactam compound represented by the formula: The &#x3b2;-lactam compound of the invention is produced by heating an aqueous solution of a salt of the &#x3b2;-lactam compound and adjusting the pH of the aqueous solution to 3 or lower. The &#x3b2;-lactam compound has excellent storage stability.

Anhydrous crystal of &#x3b2;-lactam compound and method for preparation thereof

The present invention provides novel 2&#x3b1;-methyl-2&#x3b2;-[(1,2,3-triazol-1-yl)methyl]penam-3&#x3b1;-carboxylic acid benzhydryl ester (TMPB)-acetone crystals for use in the production of 2&#x3b1;-methyl-2&#x3b2;-[(1,2,3-triazol-1-yl)methyl]penam-3&#x3b1;-carboxylic acid 1,1-dioxide benzhydryl ester (TAZB); a process for producing the TMPB-acetone crystals comprising the steps of (A) concentrating a TMPB-containing organic solvent solution, (B) dissolving the resulting concentrate in acetone, and (C) precipitating TMPB-acetone crystals from the acetone solution thus obtained; and a process for producing TAZB comprising the step of reacting the TMPB-acetone crystals with an oxidizing agent.

Penam crystals and process for producing the same

Crystals of penicillin and process for the production thereof

A process for preparing halogenated &bgr;-lactam compounds, characterized in that a &bgr;-lactam amino compound of the formula (1) is reacted with nitrous acid or nitrite in a slurry dispersion state in water, under acid condition in the presence of halogen molecules, thereby obtaining a halogenated &bgr;-lactam compound of the formula (4)

Process for producing halogenated &bgr;-lactam compound

The invention provides a process for preparing a .beta.-lactam derivative represented by the formula ##STR1## the process comprising reacting a .beta.-lactam derivative represented by the following formula (II) and having a protected carboxyl group with a cresol; ##STR2## wherein R represents a benzyl group having an electron-donating group as a substituent on the phenyl ring, a diphenylmethyl group which may have an electron-donating group as a substituent on the phenyl ring or a tert-butyl group.

Process for preparation of beta-lactam derivatives

A cephalosporin compound substituted by imidazolium ring in 3-position of cephem having the following formula (I), and pharmaceutically acceptable salt thereof, ##STR1## wherein R.sup.1 is an organic residue known in .beta.-lactam antibiotics, R.sup.2 is hydrogen atom or methoxy, n is 0 or 1, A is a nitrogen-containing group constituting imidazolium ring, is useful as an agent for preventing and treating bacterial infections.

3-Imidazolium cephalosporin derivatives

Growing community of inventors

Tokushima, Japan

Akihiro Shimabayashi