Meiji Seika Pharma Co., Ltd.

Takeshi Furuuchi

Takao Abe

Yoshiaki Sakamaki

Nakako Mitsuhashi

Yumiko Saito

Akihiro Morinaka

Seiichi Inamura

A crystalline form I of a compound represented by Formula (VII-1): having characteristic peaks appearing at lattice spacing (d) of 7.34, 5.66, 5.53, 5.30, 5.02, 4.66, 4.37, 4.28, 4.06, 3.68, 3.62, 3.47, 3.36, 3.30, 3.16, 3.11, 3.03, 2.99 and 2.50 Å in the powder X-ray diffraction pattern.

Crystalline forms of diazabicyclooctane derivative and production process thereof

A process for preparing a diazabicyclooctane compound represented by the following formula (I): wherein A represents RcO—; B represents NH or NCalkyl; C represents a benzyl group; Rc represents a Calkyl group; A is substituted with one substituent Fn1, wherein Fn1 represents an azetidine group; the process including: (a) silylating the compound represented by the following formula (IV-c): wherein in the formula (IV-c), OBn represents benzyloxy, and (b) carrying out an intramolecular urea formation reaction.

Processes for preparing a diazabicyclooctane compound

A process for preparing a diazabicyclooctane compound represented by the following formula (I): wherein A represents RcO&#x2014;; B represents NH or NCalkyl; C represents a benzyl group; Rc represents a Calkyl group; A is substituted with one substituent Fn1, wherein Fn1 represents an azetidine group; the process including: (a) silylating the compound represented by the following formula (IV-c): wherein in the formula (IV-c), OBn represents benzyloxy, and (b) carrying out an intramolecular urea formation reaction.

A crystalline form I of a compound represented by Formula (VII-1): having characteristic peaks appearing at lattice spacing (d) of 7.34, 5.66, 5.53, 5.30, 5.02, 4.66, 4.37, 4.28, 4.06, 3.68, 3.62, 3.47, 3.36, 3.30, 3.16, 3.11, 3.03, 2.99 and 2.50 &#x212b; in the powder X-ray diffraction pattern.

A process for producing a compound of the following Formula (VII-CR): The process involving providing a compound represented by the following Formula (VI): in a case where the RONHC(&#x2550;O) side chain in the compound of the Formula (VI) has a protecting group, removing the protecting group from the compound of the Formula (VI) with an acid, and adding an ester-based poor solvent to the resultant reaction solution to precipitate the compound of Formula (VII-CR), wherein in the compounds of the Formulas (VII-CR) and (VI), Ris a Calkyl or a heterocycle.

Processes for producing diazabicyclooctane compounds

A crystalline form of a diazabicyclooctane derivative represented by the following Formula (VII), and processes for producing the same: 

Beta-lactamase inhibitor and process for preparing the same

A process for producing a compound represented by a Formula (III), including reacting a compound of the following formula with a compound selected from the group consisting of 1-hydroxypyrrolidine-2,5-dione, 2-hydroxy-3a,4,7,7a-tetrahydro-1H-isoindol-1,3(2H)-dione, 2-hydroxyhexahydro-1H-isoindol-1,3(2H)-dione and 4-hydroxy-4-azatricyclo[5.2.1.0]dec-8-ene-3,5-dione, carrying out a carbonylation to obtain a compound of the following formula removing the NH protecting group P and treating the resultant compound with a base to produce a compound represented by the following formula wherein OBn is benzyloxy and Ris hydrogen, ClCO&#x2014; or ClCOCO&#x2014;.

Process for producing diazabicyclooctane derivative

A process for producing a diazabicyclooctane derivative represented by Formula (IV) and intermediates thereof by carrying out the following steps: wherein P is an NH protecting group capable of being removed with acid; Ris 2,5-dioxopyrrolidin-1-yl, 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl, 1,3-dioxohexahydro-1H-isoindol-2(3H)-yl, or 3,5-dioxo-4-azatricyclo[5.2.1.0]dec-8-en-4-yl; Ris hydrogen, ClCO&#x2014; or ClCOCO&#x2014;; Ris Calkyl or heterocyclyl, or forms a 3- to 7-membered heterocyclic ring together with the &#x2014;O&#x2014;NH&#x2014; to which it is attached; and OBn is benzyloxy.

Process for producing diazabicyclooctane derivative and intermediate thereof

A diazabicyclooctane compound, which is a beta-lactame inhibitor, represented by the following formula (I): wherein A represents Ra(Rb)N&#x2014; or RcO&#x2014;; B represents NH or NCalkyl; C represents benzyl, H or SOM, wherein M represents H, an inorganic or an organic cation; Ra and Rb represent H, Calkyl or acyl; Rc represents Calkyl or a heterocyclyl; A is unsubstituted or substituted with 0 to 4 substituents Fn1, wherein Fn1 represents Calkyl, O&#x2550;, or Rg-(CH)&#x2014;, wherein Rg represents a heterocyclyl, phenyl, heteroaryl, acyl, RdOS&#x2014;, Re(Rf)N&#x2014;, Re(Rf)NCO&#x2014;, ReO&#x2014;, ReOCO&#x2014; or a protective group, wherein Rd represents Calkyl or MO&#x2014;; Re and Rf represent H or Calkyl, and a heterocycle having at least one nitrogen atom may be formed between Ra and Rb, between Rc and B, or between Re and Rf.

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Kanagawa, Japan

Takeshi Furuuchi