JP5842191B2 - ベンジルベンゼンsglt2阻害剤の結晶形 - Google Patents
ベンジルベンゼンsglt2阻害剤の結晶形 Download PDFInfo
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- JP5842191B2 JP5842191B2 JP2013513540A JP2013513540A JP5842191B2 JP 5842191 B2 JP5842191 B2 JP 5842191B2 JP 2013513540 A JP2013513540 A JP 2013513540A JP 2013513540 A JP2013513540 A JP 2013513540A JP 5842191 B2 JP5842191 B2 JP 5842191B2
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- 230000000304 vasodilatating effect Effects 0.000 description 1
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- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- XOSKJKGKWRIMGV-DGCLKSJQSA-N way-163909 Chemical compound C1NCCN2[C@@H]3CCC[C@@H]3C3=CC=CC1=C32 XOSKJKGKWRIMGV-DGCLKSJQSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
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Description
本出願は、2010年6月12日に出願されたPCT/CN2010/073865に基づいて優先権を主張し、その全体をあらゆる目的のために本明細書中に援用する。
I.定義
本明細書で使用される場合、用語「治療すること」及び「治療」は、当該用語が適用される疾患若しくは症状、又は当該疾患若しくは症状の1以上の症状の発症を遅延させるか、その進行を遅延若しくは覆すか、又はそれらを緩和若しくは予防することを指す。
II.結晶形
III.結晶形の生成方法
(a)無定形(2S,3R,4R,5S,6R)‐2‐(4‐クロロ‐3‐(4‐(2‐シクロプロポキシエトキシ)ベンジル)フェニル)‐6‐(ヒドロキシメチル)テトラヒドロ‐2H‐ピラン‐3,4,5‐トリオールと好適な溶剤を撹拌しながら混ぜ合わせて溶液を形成し;(b)沈殿溶媒を前記溶液に添加して混合物を提供し;そして(c)ステップ(b)の混合物から前記結晶形を単離すること、を含んで成る方法を提供する。
IV.医薬組成物
V.使用の方法
以下の実施例は、例示的目的で提供されており、本発明をいかなる方法においても制限することを意図してない。当業者であれば、本質的に同じ結果を得るために、変更又は改変することができる様々な重大でないパラメーターを容易に理解するであろう。
(2S,3R,4S,5S,6R)‐2‐(4‐クロロ‐3‐(4‐(2‐シクロプロポキシエトキシ)ベンジル)フェニル)‐6‐(ヒドロキシメチル)‐2‐メトキシテトラヒドロ‐2H‐ピラン‐3,4,5‐トリオール(5)の調製
(2S,3R,4S,5S,6R)‐2‐(4‐クロロ‐3‐(4‐(2‐シクロプロポキシエトキシ)ベンジル)フェニル)‐6‐(ヒドロキシメチル)テトラヒドロ‐2H‐ピラン‐3、4,5‐トリオール、ビス(L‐プロリン)錯体(7)の調製
この実施例は、(2S,3R,4S,5S,6R)‐2‐(4‐クロロ‐3‐(4‐(2‐シクロプロポキシエトキシ)ベンジル)フェニル)‐6‐(ヒドロキシメチル)テトラヒドロ‐2H‐ピラン‐3、4,5‐トリオールの結晶形の調製を例示する。
この実施例は、結晶性(2S,3R,4S,5S,6R)‐2‐(4‐クロロ‐3‐(4‐(2‐シクロプロポキシエトキシ)ベンジル)フェニル)‐6‐(ヒドロキシメチル)テトラヒドロ‐2H‐ピラン‐3,4,5‐トリオールを調製するための代替条件を例示する。
手順A:
手順B:
約100mgの結晶性化合物(8)を、約60℃にて最少量の溶媒で溶解した。溶液を、濾過し、そして2つの部分に分け、一方の部分を氷浴中で冷やし、そしてかき混ぜた(急)、そして他方を、外気及び外気温にさらすことによって冷ました(緩)。固体を、濾過によって回収し、乾燥させ、そしてXRPDによって分析した。以下の表には、再結晶化の溶媒と結果をまとめある。形成された結晶のすべてが、出発物質のXRPDと同一である。
粉末形態の結晶性化合物(8)の吸湿性の傾向を、25℃にて最長10日間、75%と92.5%の相対湿度で試験した。試薬には:(1)水:社内、MilliQ、18.2MΩ;(2)NaCl:ARグレード;(3)KNO3:ARグレード;(4)25℃/75%RHを制御するための、過剰なNaCl固体を含む飽和NaCl溶液;及び(5)25℃/92.5%RHを制御するための、過剰なKNO3固体を含む飽和KNO3溶液、が含まれる。器具には、(1)デシケータ、240mmのID;及び(2)蓋付き秤量瓶:50mmのID×30mmの高さ、が含まれる。
実施例12.結晶性化合物(8)を含有するカプセルの調製
Claims (33)
- さらに、5.4, 11.3, 11.9, 16.3, 20.6, 21.2, 22.8, 23.0, 23.4, 23.6, 23.9, 24.7, 25.4, 25.8, 27.8及び28.2 ° 2θ (± 0.1 °2θ)に1又は複数のピークがあるX線粉末回折(XRPD)パターンにより特徴づけられ、当該XRPDがCuKα1線を用いて行われる、請求項1に記載の結晶形。
- 11.2, 12.9, 15.5, 17.8, 19.1, 20.0, 20.6, 20.7, 21.2, 及び22.8 ° 2θ (± 0.1 °2θ)にピークがあるX線粉末回折(XRPD)パターンにより特徴づけられ、当該XRPDがCuKα1線を用いて行われる、請求項2に記載の結晶形。
- 5.4, 11.2, 11.9, 12.9, 15.5, 16.3, 17.8, 19.1, 20.6, 及び20.7° 2θ (± 0.1 °2θ)にピークがあるX線粉末回折(XRPD)パターンにより特徴づけられ、当該XRPDがCuKα1線を用いて行われる、請求項2に記載の結晶形。
- 図2のピークと実質的に一致するXRPDピークにより特徴づけられる、請求項1に記載の結晶形。
- 約353, 688, 825, 1178, 1205, 1212, 1608, 2945, 3010 及び 3063 cm-1に1又は複数のピークがあるラマンスペクトルにより特徴づけられる、請求項1に記載の結晶形。
- 約353, 688, 及び 825 cm-1にピークがあるラマンスペクトルにより特徴づけられる、請求項1に記載の結晶形。
- 図4のピークと実質的に一致するラマンピークにより特徴づけられる、請求項1に記載の結晶形。
- さらに、5.4, 11.3, 11.9, 16.3, 20.6, 21.2, 22.8, 23.0, 23.4, 23.6, 23.9, 24.7, 25.4, 25.8, 27.8 及び 28.2° 2θ (± 0.1 °2θ)に1又は複数のピークがあるXRPDパターン、ここで、当該XRPDはCuKα1線を用いて行われる;並びに
353, 688, 825, 1178, 1205, 1212, 1608, 2945, 3010 及び 3063 cm-1に1又は複数のピークがあるラマンスペクトル、により特徴づけられる、請求項1に記載の結晶形。 - さらに、20.6, 21.2, 22.8 及び 28.2° 2θ (± 0.1 °2θ)に1又は複数のピークがあるXRPDパターン、ここで、当該XRPDはCuKα1線を用いて行われる;並びに
353, 688, 及び825 cm-1に1又は複数のピークがあるラマンスペクトル、により特徴づけられる、請求項9に記載の結晶形。 - 約136℃の示差走査熱量計測(DSC)吸熱により特徴づけられる、請求項1に記載の結晶形。
- 図7と実質的に一致する単位格子データにより特徴づけられる、請求項1に記載の結晶形。
- 医薬として許容される賦形剤及び請求項1に記載の化合物の結晶形を含んで成る医薬組成物。
- 同位体標識されている、請求項1に記載の化合物の結晶形。
- 請求項1に記載の化合物の結晶形の生成方法であって、以下の工程:
(a)(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオール ビス(L−プロリン)錯体と、メタノール及びエタノールからなる群より選択される溶媒とを撹拌しながら混ぜ合わせて溶液を形成し;
(b)水を前記溶液に添加して混合物を提供し;そして
(c)前記混合物から前記結晶形を単離すること、
を含んで成る、方法。 - 工程(a)の溶媒がメタノールである、請求項15に記載の方法。
- 工程(b)の前記混合物中のメタノール:水の比率が体積当たり約1:1〜約1:9である、請求項15に記載の方法。
- 工程(b)の前記混合物中のメタノール:水の比率が体積当たり約1:5である、請求項15に記載の方法。
- 工程(b)の前記混合物中の錯体:溶媒及び水の比率が約1:10〜約1:25(w/v)である、請求項15に記載の方法。
- 工程(b)の前記混合物が塩基を更に含んで成る、請求項15に記載の方法。
- 工程(b)の前記混合物が塩を更に含んで成る、請求項15に記載の方法。
- 工程(b)の前記混合物が請求項1に記載の化合物の種晶を更に含んで成る、請求項18に記載の方法。
- 請求項1に記載の化合物の結晶形の生成方法であって、以下の工程:
(a)(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールと、メタノール及びエタノールからなる群から選択される溶媒とを撹拌しながら混ぜ合わせて溶液を形成し;そして
(b)前記溶液から前記結晶形を単離すること、
を含んで成る、方法。 - 以下の工程:
(a)無定形(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールと、メタノール及びエタノールからなる群より選択される溶媒とを撹拌しながら混ぜ合わせて溶液を形成し;そして
(b)水を前記溶液に添加して混合物を提供し;そして
(c)前記混合物から前記結晶形を単離すること、
を含んで成る、請求項23に記載の方法。 - 水を前記溶液に添加することを更に含んで成る、請求項23に記載の方法。
- 工程(a)の溶媒がメタノールである、請求項25に記載の方法。
- 工程(b)の前記混合物中のメタノール:水の比率が体積当たり約1:1〜約1:9である、請求項25に記載の方法。
- 工程(b)の前記混合物中のメタノール:水の比率が体積当たり約1:5である、請求項25に記載の方法。
- 工程(b)の前記混合物中の錯体:溶媒及び沈殿溶媒の比率が約1:1〜約1:9である、請求項24に記載の方法。
- 工程(b)の前記混合物が請求項1に記載の化合物の種晶を更に含んで成る、請求項24に記載の方法。
- 前記(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールが無定形(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールである、請求項25に記載の方法。
- (a2)(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオール ビス(L−プロリン)錯体と酢酸エチル及び水との混合物とを撹拌しながら混ぜ合わせて溶液を形成し;そして
(a3)工程(a2)の前記溶液から無定形(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールを単離すること、
により、無定形(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオールが(2S,3R,4R,5S,6R)−2−(4−クロロ−3−(4−(2−シクロプロポキシエトキシ)ベンジル)フェニル)−6−(ヒドロキシメチル)テトラヒドロ−2H−ピラン−3,4,5−トリオール ビス(L−プロリン)から調製される、請求項31に記載の方法。 - SGLT2を阻害することにより影響を受ける疾患又は症状を治療するための組成物であって、請求項1に記載の化合物の結晶形を含んで成り、前記疾患又は症状が、1型糖尿病、2型糖尿病、高血糖症、糖尿病性合併症、インスリン耐性、メタボリック・シンドローム、高インスリン血症、高血圧、高尿酸血症、肥満、浮腫、脂質異常症、慢性心疾患、アテローム性動脈硬化症、及び癌、から成る群から選択される、組成物。
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