JP2013216710A - リファキシミンの新規多形、その製造方法、及び医薬製剤中でのその使用 - Google Patents
リファキシミンの新規多形、その製造方法、及び医薬製剤中でのその使用 Download PDFInfo
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Abstract
【解決手段】本発明の対象は、経口用および局所用のリファキシミンを含む医薬製剤の製造において有用であると共に、粗リファキシミンをエチルアルコールに加熱溶解すること、水を定められた温度で定められた時間加えることにより生成物の結晶化を引き起こすこと、および続いて、最終生成物中の設定含水量に至るまで制御条件下に乾燥することにより実施される結晶化プロセスにより得られる、リファキシミンδおよびリファキシミンεと呼ばれる抗生物質リファキシミン(INN)の結晶多形である。
【選択図】図1
Description
リファキシミン(INN;メルクインデックス,XIII版,8304を参照)は、リファマイシンクラスに属する抗生物質であって、まさに、これは伊国特許IT1154655号に説明され請求項に記載されているピリド−イミダゾ・リファマイシンである。一方、欧州特許EP0161534号には、リファマイシンO(メルクインデックス,XIII版,8301)から出発してそれを製造するための方法が説明され請求項に記載されている。
既述のように、本発明の対象は、リファキシミン(INN)として知られている抗生物質のδ形とε形、その製造方法、および経口または局所用の医薬製剤の製造におけるそれらの使用である。
X線管:銅
用いた放射線:K(α1)、K(α2)
発電機の電圧および電流:KV40,mA40
モノクロメーター:グラファイト
ステップサイズ:0.02
ステップ当たりの時間:1.25秒
出発および最終角2θ値:3.0°÷30.0°
分析サンプル中に存在する水含量の評価は、常に、Karl Fisher法で行った。
<実施例1>
(粗リファキシミンおよび乾燥粗リファキシミンの調製)
メカニカルスターラー、温度計および還流冷却器を備える三つ口フラスコに、室温で、脱塩水120ml、エチルアルコール96ml、リファマイシンO63.5gおよび2−アミノ−4−メチルピリジン27.2gを順次仕込む。仕込んだ後、その物(mass)を47±3℃で加熱し、この温度で5時間攪拌を続け、次に、20±3℃まで冷却し、脱塩水9ml、エチルアルコール12.6ml、アスコルビン酸1.68gおよび濃塩酸9.28gからなる別途調製された混合物を、30分間で加える。添加終了時、その物を20±3℃の内部温度で30分間攪拌を続け、次に、同じ温度で、濃塩酸7.72gをpHが2.0になるまで滴下する。
<実施例2>
(リファキシミンεの調製)
実施例1を繰り返してδ形を得た後、固体粉末をさらに減圧下に温度65℃で24時間乾燥する。得られた生成物は、7.0°±0.2、7.3°±0.2、8.2°±0.2、8.7°±0.2、10.3°±0.2、11.1°±0.2、11.7°±0.2、12.4°±0.2、14.5°±0.2、16.3°±0.2、17.2°±0.2、18.0°±0.2、19.4°±0.2の角度2θの値においてピークを示す粉末X線ディフラクトグラムを特徴とするリファキシミンεである。
<実施例3>
(経口投与によるイヌでの生物学的利用可能性)
20週齢で5.0〜7.5kgの8匹の純血種ビーグルメスイヌを、4匹ずつの2つのグループに分けた。
Cmax=血漿中のリファキシミンの観察された最大血漿濃度
Tmax=Cmaxが達成される時間
AUC=線形台形公式により計算された濃度−時間曲線における面積
表1に報告された結果は、実際に吸収されないリファキシミンεに対し、いかにリファキシミンδが吸収されるか(40倍以上)を明確に示している。
Claims (17)
- 5.7°±0.2、6.7°±0.2、7.1°±0.2、8.0°±0.2、8.7°±0.2、10.4°±0.2、10.8°±0.2、11.3°±0.2、12.1°±0.2、17.0°±0.2、17.3°±0.2、17.5°±0.2、18.5°±0.2、18.8°±0.2、19.1°±0.2、21.0°±0.2、21.5°±0.2の回折角2θの値にパターンピークを示す粉末X線ディフラクトグラムを特徴とする、リファキシミンの多形結晶δ。
- 含水量が3.0%(w/w)〜4.5%(w/w)である請求項1記載のリファキシミンの多形結晶δ。
- 7.0°±0.2、7.3°±0.2、8.2°±0.2、8.7°±0.2、10.3°±0.2、11.1°±0.2、11.7°±0.2、12.4°±0.2、14.5°±0.2、16.3°±0.2、17.2°±0.2、18.0°±0.2、19.4°±0.2の回折角2θの値にパターンピークを示す粉末X線ディフラクトグラムを特徴とする、リファキシミンの多形結晶ε。
- 水とエチルアルコールとの1:1〜2:1の体積比の混合溶媒中、1モル当量のリファマイシンOを、過剰量の2−アミノ−4−メチルピリジンと、40℃〜60℃の温度で2〜8時間反応させること、その反応物を、室温で、水、エチルアルコールおよび濃塩酸の混合物中でアスコルビン酸溶液で処理すること、その反応物を濃塩酸によりpHを2.0にすること、懸濁液を濾過すること、得られた固体を前記反応で用いたものと同じ水/エチルアルコール混合溶媒で洗うこと、および、このように得られた固体粗リファキシミンを、含水量が2.5%(w/w)〜6.0%(w/w)になるまで乾燥することを特徴とする、リファキシミン結晶多形δの製造方法。
- 粗リファキシミンを、45℃〜65℃の温度でエチルアルコールに溶解し、水を加えることにより沈澱を引き起こし、懸濁液の温度を28℃〜32℃の間の値まで下げて結晶化を開始させ、そのようにして得られた懸濁液を攪拌下に40℃〜50℃に6〜24時間保ち、次に、0℃に15分〜1時間冷却してから濾過し、得られた固体を水で洗浄し、固体の乾燥を行うことを特徴とする請求項4記載の製造方法。
- 1モル当量のリファマイシンOに対する2−アミノ−4−メチルピリジンの使用量が2.0〜3.5モル当量である請求項4又は5記載の製造方法。
- 粗リファキシミンをエチルアルコールに溶解した後、その溶解に用いたエチルアルコールの重量に対して15%〜70%の重量の水を加えることにより沈澱を引き起こす請求項5記載の製造方法。
- 含水量が3.0%〜4.5%になるまで乾燥する請求項4〜7のいずれかに記載の製造方法。
- 減圧下または大気圧で室温または高温で乾燥剤の存在下または不存在下に6〜24時間、請求項1記載のリファキシミン多形結晶δを乾燥することにより、7.0°±0.2、7.3°±0.2、8.2°±0.2、8.7°±0.2、10.3°±0.2、11.1°±0.2、11.7°±0.2、12.4°±0.2、14.5°±0.2、16.3°±0.2、17.2°±0.2、18.0°±0.2、19.4°±0.2の回折角2θの値にパターンピークを示す粉末X線ディフラクトグラムを有するリファキシミンの多形結晶εを得ることを特徴とする、リファキシミン多形結晶εを製造する方法。
- 水とエチルアルコールとの1:1〜2:1の体積比の混合溶媒中、1モル当量のリファマイシンOを、過剰量の2−アミノ−4−メチルピリジンと、40℃〜60℃の温度で2〜8時間反応させ、
その反応物を、室温で、水、エチルアルコールおよび濃塩酸の混合物中でアスコルビン酸溶液で処理し、
その反応物を濃塩酸によりpHを2.0にし、
懸濁液を濾過し、
得られた固体を前記反応で用いたものと同じ水/エチルアルコール混合溶媒で洗い、
固体粗リファキシミンを含水量が2.5%(w/w)〜6.0%(w/w)になるまで乾燥する
ことにより得られるリファキシミン多形結晶δ。 - 減圧下または大気圧で室温または高温で乾燥剤の存在下または不存在下に6〜24時間、請求項1、2又は10記載のリファキシミン多形結晶δを乾燥して結晶形を転化させることにより得られるリファキシミン多形結晶ε。
- 薬学的に許容可能な賦形剤と、請求項1、2もしくは10記載のリファキシミン多形結晶δ、又は請求項3もしくは11記載のリファキシミン多形結晶εとを含む医薬製剤。
- 固形製剤である請求項12記載の医薬製剤。
- 錠剤、硬質および軟質ゼラチンカプセル、糖衣丸剤、トローチ、オブラート、ペレット、又は密封包装中の粉末の形態である請求項12又は13記載の医薬製剤。
- 経口用である請求項12〜14のいずれかに記載の医薬製剤。
- 軟膏、ポマード、クリーム、ゲル又はローションの形態である請求項12記載の医薬製剤。
- 請求項1、2若しくは10記載のリファキシミン多形結晶δ、又は請求項3若しくは11記載のリファキシミン多形結晶εを含む局所用の医薬製剤。
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EP05004695.2A EP1698630B1 (en) | 2005-03-03 | 2005-03-03 | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations |
EP05004695.2 | 2005-03-03 |
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US7048906B2 (en) | 1995-05-17 | 2006-05-23 | Cedars-Sinai Medical Center | Methods of diagnosing and treating small intestinal bacterial overgrowth (SIBO) and SIBO-related conditions |
US6861053B1 (en) | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
US7902206B2 (en) | 2003-11-07 | 2011-03-08 | Alfa Wassermann, S.P.A. | Polymorphic forms α, β and γ of rifaximin |
US7906542B2 (en) | 2004-11-04 | 2011-03-15 | Alfa Wassermann, S.P.A. | Pharmaceutical compositions comprising polymorphic forms α, β, and γ of rifaximin |
ITMI20032144A1 (it) | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
DK1698630T3 (da) | 2005-03-03 | 2014-12-08 | Alfa Wassermann Spa | Nye polymorfe former af rifaximin, fremgangsmåde for deres fremstilling og anvendelse deraf i de medicinske præparater |
ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
ITMI20061692A1 (it) | 2006-09-05 | 2008-03-06 | Alfa Wassermann Spa | Uso di polioli per ottenere forme polimorfe stabili di rifaximina |
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