JP2008531623A - 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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- JP2008531623A JP2008531623A JP2007557398A JP2007557398A JP2008531623A JP 2008531623 A JP2008531623 A JP 2008531623A JP 2007557398 A JP2007557398 A JP 2007557398A JP 2007557398 A JP2007557398 A JP 2007557398A JP 2008531623 A JP2008531623 A JP 2008531623A
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- Prior art keywords
- rifaximin
- water
- temperature
- ethyl alcohol
- suspension
- Prior art date
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- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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Abstract
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。
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。
(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。
(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。
(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。
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 (11)
- 2.5%(w/w)〜6%(w/w)、好ましくは3.0%〜4.5%の含水量、および、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δと呼ばれる抗生物質リファキシミンの多形。
- 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と呼ばれる抗生物質リファキシミンの多形。
- 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、好ましくは2.0〜3.5モル当量の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、好ましくは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し、懸濁液の温度を攪拌下に50℃〜0℃の間の値に4〜36時間低下させ、最後に、懸濁液を濾過し、得られた固体を水で洗い、減圧下または常圧条件下に乾燥剤を用いてまたは用いることなく室温〜105℃の温度で2〜72時間乾燥させることにより精製することを特徴とする、リファキシミンδおよびεの製造方法。
- 粗リファキシミンのエタノール溶液に水を加えた後、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、得られた固体を含水量が2.5%(w/w)〜6%(w/w)、好ましくは3.0%〜4.5%になるまで乾燥する、リファキシミンδの製造のための請求項3に記載の方法。
- 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リファキシミンδを乾燥するが、乾燥は、ε形への転化が達成されるのに必要な時間まで延長される、リファキシミンεの製造のための請求項3に記載の方法。
- 希釈剤、結合剤、潤滑剤、崩壊剤、着色剤、風味剤および甘味剤のような通常の賦形剤と一緒の、抗生活性を有する経口用の医薬製剤の調製における、リファキシミンδの使用。
- 希釈剤、結合剤、潤滑剤、崩壊剤、着色剤、風味剤および甘味剤のような通常の賦形剤と一緒の、抗生活性を有する経口用の医薬製剤の調製における、リファキシミンεの使用。
- 経口用の製剤が、被覆および非被覆錠剤、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、および密封包装中の粉末から選択される、請求項6または7に記載の使用。
- 局所用の抗生活性を有する医薬製剤の調製におけるリファキシミンδの使用。
- 局所用の抗生活性を有する医薬製剤の調製におけるリファキシミンεの使用。
- 局所用の製剤が、軟膏、ポマード、クリーム、ゲルおよびローションから選択される請求項9または10に記載の使用。
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EP05004695.2 | 2005-03-03 | ||
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