JP2010511602A - 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶形 - Google Patents
1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶形 Download PDFInfo
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- JP2010511602A JP2010511602A JP2009538905A JP2009538905A JP2010511602A JP 2010511602 A JP2010511602 A JP 2010511602A JP 2009538905 A JP2009538905 A JP 2009538905A JP 2009538905 A JP2009538905 A JP 2009538905A JP 2010511602 A JP2010511602 A JP 2010511602A
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- Prior art keywords
- methyl
- fluorophenyl
- glucopyranosyl
- thienylmethyl
- benzene
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
で示される1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼンが記載されている。
1. 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶;
2. CuKα放射を用いて測定された粉末X線回折パターンが、以下の2θ値を含む、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶:4.36 ± 0.2, 13.54 ± 0.2, 16.00 ± 0.2, 19.32 ± 0.2, 20.80 ± 0.2;
3. X線粉末回折パターンが図1に示されたものと実質的に同一である、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶;
4. IRスペクトルが図2に示されたものと実質的に同一である、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶;
5. 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼンの溶液を形成し、そして該溶液から沈殿または再結晶によりその1/2水和物を結晶化することからなる、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶の製造方法;
6. 有効量の1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶および薬理的に許容しうる担体を含む医薬組成物;
7. 糖尿病、糖尿病性網膜症、糖尿病性神経障害、糖尿病性腎症、遅延創傷治癒、インスリン抵抗性、高血糖症、高インスリン血症、高脂肪酸血症、高グリセロール血症、高脂血症、肥満症、高トリグリセリド血症、X症候群、糖尿病性合併症、アテローム硬化症または高血圧症の処置または進行もしくは発症を遅延させる方法であって、治療有効量の1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶を投与することを含む方法。
本発明の化合物(I)の結晶形は、X線粉末回折パターンにより特徴付けられる。化合物(I)の1/2水和物の結晶のX線回折パターンは、CuKα放射を用いて測定するX線回折計(RINT-TTR III、リガク、東京、日本)で測定した。X線粉末回折の方法は、以下の通りである:
走査速度: 2.00度/分。
ターゲット: CuKα。
電圧: 50kV。
電流: 300mA。
走査範囲: 3〜40.0度
サンプリング幅: 0.0200度。
鉱物油における本発明の結晶形の赤外線スペクトルは、以下の主なピークを含む:1626,1600,1549,および1507cm−1。
本発明の結晶形は、1/2水和物の形態で存在することが観察された。本発明の結晶形の理論的含水量は、1.98%である。本発明の結晶の熱重量分析は、1.705%の質量損失を示す。
WO2005/012326に記載されたのと同様の方法で、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼンを調製した。
1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン(1.62g)のアモルファス粉末を、アセトン(15ml)に溶解し、そこにH2O(30ml)および種結晶を加えた。混合物を室温で18時間攪拌し、沈殿物を収集し、アセトン−H2O(1:4、30ml)で洗浄し、減圧下、室温で乾燥させ、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物(1.52g)を無色の結晶として得た。mp 97-100℃.
Claims (7)
- 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶。
- CuKα放射を用いて測定された粉末X線回折パターン以下の2θ値を含む、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶:4.36 ± 0.2, 13.54 ± 0.2, 16.00 ± 0.2, 19.32 ± 0.2, 20.80 ± 0.2。
- X線粉末回折パターンが図1に示されたものと実質的に同一である、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶。
- IRスペクトルが図2に示されたものと実質的に同一である、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶。
- 1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼンの溶液を形成し、そしてその溶液から沈殿または再結晶により該1/2水和物を結晶化することからなる、1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶の製造方法。
- 有効量の1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶および薬理的に許容しうる担体を含む医薬組成物。
- 糖尿病、糖尿病性網膜症、糖尿病性神経障害、糖尿病性腎症、遅延創傷治癒、インスリン抵抗性、高血糖症、高インスリン血症、高脂肪酸血症、高グリセロール血症、高脂血症、肥満症、高トリグリセリド血症、X症候群、糖尿病性合併症、アテローム硬化症または高血圧症の処置または進行もしくは発症を遅延させる方法であって、治療有効量の1−(β−D−グルコピラノシル)−4−メチル−3−[5−(4−フルオロフェニル)−2−チエニルメチル]ベンゼン1/2水和物の結晶を投与することを含む方法。
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