Kaneka Corporation

Kanegafuchi Chemical Industry Co., Ltd.

Teruyoshi Koga

Keita Nishino

Yasuyoshi Ueda

Kenji Inoue

Satomi Takahashi

Noboru Ueyama

Masafumi Fukae

Takao Yamaguchi

Shigeo Hayashi

Yoshihisa Okamoto

A reduced coenzyme Qderivative represented by formula (1), wherein Rand Rare each independently H or an alkoxycarbonyl group represented by formula (2), and at least one of them is an alkoxycarbonyl group represented by the formula (2); in the formula (2), Ris an optionally substituted linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, or an optionally substituted heteroaryl group having 4 to 20 carbon atoms, and when Ris a group substituted with polyethylene glycol, the molecular weight of the polyethylene glycol is not more than 300.

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The present invention relates to a method for crystallization of (2R)-2-{(3S,4S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl}propionic acid, and is characterized in that crystallization is carried out by mixing a solution containing the compound with a substituted aromatic hydrocarbon solvent and/or a halogenated hydrocarbon solvent. The method can provide a crystal of the compound with a high purity and a high yield while the content of 2S isomer is kept at a low level.

Method for crystallization of azetidinonecarboxylic acid

An improved crystallization method for an azetidinone compound represented by the formula 1: 

Crystallization method for intermediates of carbapenem antibiotics

The present invention provides a novel intermediate represented by formula (1), (3), or (4) for efficiently producing a 1&#x3b2;-methylcarbapenem compound for oral administration, and a process for producing the intermediate. That is, the present invention provides a process for producing a novel &#x3b2;-lactam compound represented by formula (4), the process including allowing a &#x3b2;-lactam compound represented by formula (5) as a starting material to react with a compound represented by formula (6) in the presence of a base to obtain a novel &#x3b2;-lactam compound represented by formula (1), protecting the hydroxyl group, subsequently performing cyclization in the presence of a strong base, allowing the cyclized compound to react with diphenylphosphoryl chloride to obtain a novel &#x3b2;-lactam compound represented by formula (3), and eliminating the protecting group therefrom. The formulae referred to are diagrammed as follows: (In the formulae, Rrepresents a trimethylsilyl group or a triethylsilyl group; Rrepresents an aryl group or a heteroaryl group; Rrepresents an aryl group or a heteroaryl group; Rrepresents an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms; and X represents a halogen atom.)

Intermediate for carbapenem compound for oral administration and process for producing the same

The present invention provides a process for efficiently producing a 1&#x3b2;-methylcarbapenem compound for oral administration. The process, which is for producing a 1&#x3b2;-methylcarbapenem compound represented by general formula (2), is characterized by reacting a &#x3b2;-lactam compound represented by general formula (1) as a starting material with a thiol compound (R&#x2014;SH) in the presence of a base and optionally eliminating the protective group R. In the formulae (1) and (2), Rdenotes a hydrogen atom, a trimethylsilyl group or a triethylsilyl group; Rdenotes an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms; Rdenotes an organic group; and Rdenotes hydrogen, a trimethylsilyl group or a triethylsilyl group.

Process for producing carbapenem compound for oral administration

A novel 2,4-dihydroxyadipic acid derivative of the formula: ##STR1## wherein R.sup.1 and R.sup.4 are the same or different and each a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a silyl group, and R.sup.2 and R.sup.3 are the same or different and each a hydrogen atom or a protective group of a hydroxy group or together form a ring, which is useful as a common intermediate in the synthesis of HMG-CoA reductase inhibitor.

2,4-dihydroxyadipic acid derivative

A malonic monoester is prepared in a good yield by a single step reaction by reacting malonic acid with an alcohol in the presence of a base and an activator of malonic acid selected from the group consisting of an acyl halide or halocarbonate and an acid anhydride or dicarbonate.

Growing community of inventors

Takasago, Japan

Teruyoshi Koga