JP5663750B2 - 難溶性物質の水溶解性改善方法 - Google Patents
難溶性物質の水溶解性改善方法 Download PDFInfo
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- JP5663750B2 JP5663750B2 JP2011534048A JP2011534048A JP5663750B2 JP 5663750 B2 JP5663750 B2 JP 5663750B2 JP 2011534048 A JP2011534048 A JP 2011534048A JP 2011534048 A JP2011534048 A JP 2011534048A JP 5663750 B2 JP5663750 B2 JP 5663750B2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K9/00—Medicinal preparations characterised by special physical form
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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Description
抗生物質としては、アミカシン、ディベカシン、ゲンタマイシン、バシトラシン、ペニシリン、セファレキシン、テトラサイクリン、ストレプトマイシン、ナイスタチン、エリスロマイシン、硫酸フラジオマイシン、クロラムフェニコール、セフメタゾール、トルナフテート等を例示することができる。
抗菌剤としては、オフロキサシン、塩酸シプロフロキサシン、トシル酸トスフロキサシン、ノルフロキサシン、塩酸ロメフロキサシン、パズフロキサシン、ロキタマイシン、セフポドキシムプロキセチル、ロキシスロマイシン、酢酸ミデカマイシン、セファトリジン、プロピオン酸ジョサマイシン、ホスホマイシン又はその塩等を例示することができる。
精神安定剤としては、ジアゼパム、ロラゼパム、オキサゾラム等が挙げられる。
抗てんかん剤としては、フェニトイン、フェノバルビタール、カルバマゼピン、プリミドン、フェナセミド、エチルフェナセミド、エトトイン、フエンサクシミド、ニトラゼバン、クロナゼバン等を例示することができる。
抗うつ剤としては、イミプラニン、ノキシプチリン、フェネルジン等を例示することができる。
アレルギー性疾患治療剤としては、フマル酸クレマスチン、塩酸シプロヘプタジン、塩酸フェキソフェナジン、エバスチン、メキタジン、ジフェンヒドラミン、メトジラミン、クレミゾール、メトキシフェナミン等を例示することができる。
高血圧治療剤としては、アラセプリル、塩酸ニカルジピン、塩酸デラプリル、カプトプリル、シルニジピン、フェロジピン、塩酸バルニジピン、塩酸エホニジピン、ベシル酸アムロジピン、塩酸ベニジピン、ニソルジピン、塩酸マニジピン、ニトレンジピン、ニルバジピン、トランドラプリル、バルサルタン、カンデサルタンシレキセチル、ウラピジル、カルベジロール、塩酸プラゾシン、塩酸ブナゾシン、メシル酸ドキサゾシン、レセルピン、メチルドパ、酢酸グアナベンズ、デセルピジン、メプタメ、メプタメート等を例示することができる。
血行促進剤としては、酢酸トコフェロール、ニコチン酸ベンジルエステル、トラゾリン、ベラパミル、カフェイン、シクランデレート、アセチルコリン、ニコチン酸トコフェロール等を例示することができる。
糖尿病治療剤としては、トルブタミド、グリベンクラミド、グリクラジド、トログリタゾン、エパルレスタット、ブフォルミン、メトフォルミン等を例示することができる。
ホルモン剤としては、デキサメタゾン、酢酸デキサメタゾン、ベタメタゾン、吉草酸ベタメタゾン、ジプロピオン酸ベタメタゾン、プロピロン酸ベクロメタゾン、プレドニゾロン、吉草酸プレドニゾロン、酢酸プレドニゾロン、メチルプレドニゾロン、酢酸メチルプレドニゾロン、ヒドロコルチゾン、酢酸ヒドロコルチゾン、酢酸プロピオン酸ヒドロコルチゾン、アムシノニド、トリアムシノロン、トリアムシノロンアセトニド、フルオシノロンアセトニド、ヘキセストロール、メチマゾール、エストリオール、プロピオン酸エストリオール、酢酸クロベタゾン、プロピオン酸クロベタゾール、フルオシノニド、プロピオン酸テストステロン、エナント酸テストステロン、フルオキシメステロン、プロピオン酸ドロモスタノロン、安息香酸エストラジオール、プロピオン酸エストラジオール、吉草酸エストラジオール、エチニルエストラジオール、メストラノール、安息香酸酢酸エストリオール、フルオロメトロン、フルドロキシコルチド、吉草酸ジフルコルトロン、ハルシノニド、プロゲステロン、カプロン酸ヒドロキシプロゲステロン、プレグナンジオール、酢酸メドロキシプロゲステロン、ジメチステロン、ノルエチステロン、アリルエストレノール、カプロン酸ゲストノロン、オキセンドロン等を例示することができる。
強心用薬剤としては、ジゴキシン、ジゴトキシン、ユビデカレノン等を例示することができる。
不整脈用薬剤としては、ピンドロール、ナドロール、マロン酸ボピンドロール、塩酸アロチノロール、アテノロール、リドカイン、塩酸プロパフェノン、塩酸アミオダロン、ジソピラミド、塩酸カルテオロール等を例示することができる。
利尿用薬剤としては、ポリチアジド、スピロノラクトン、クロルタリドン、トリアムテレン、ヒドロクロロチアジド、フロセミド等を例示することができる。
局所麻酔剤としては、塩酸ジプカイン、アミノ安息香酸エチル、塩酸プロカイン、リドカイン、塩酸テトラカイン、塩酸リドカイン、テーカイン、ベゾカイン、ベンジルアルコール、塩酸プラモキシン、塩酸カタカイン、塩酸ブタニカイン、塩酸ピペロカイン、クロロブタノール等を例示することができる。
難溶性植物生長調節物質としては、6−ベンジルアミノプリン、シクラニリド、フルメトラリン、ホルクロルフェニュロン、イナベンフィド、2−(1−ナフチル)アセトアミド、パクロブトラゾール、N−フェニルフタルアミド酸、チジアズロン、ウニコナゾール等を例示することができる。
A.[ハイドロキシアパタイトの調製]
攪拌下の水酸化カルシウム懸濁液に、30重量%濃度のリン酸水溶液を、Ca/P比が1.67になるまで滴下した。このようにして生成したゲル状物質を室温で1日間放置して熟成した。その後、かかるゲル状物質をガラスフィルターで濾過し、残った物質をさらに100℃の空気中で乾燥し、ミキサーで粉砕して、ハイドロキシアパタイトを得た。
上記[ハイドロキシアパタイトの調製]で得たハイドロキシアパタイト(以下、単に「ハイドロキシアパタイト」という。)を、ジェットミル(Co−Jetシステムα−mkII 株式会社セイシン企業製)で微粉砕し、乾式法によるハイドロキシアパタイト微粒子を得た。
ハイドロキシアパタイト、リン酸三カルシウム、及び炭酸カルシウムを20%の懸濁液になるように水に懸濁した。これをダイノーミル(ECM-PILOT Willy A. Baechofen AG Machinenfabrik Basel社製)にて0.3mmのジルコニアビーズを用いて粉砕した。30分毎に粒度分布を測定し、ほとんど粒子径に変化が見られなかった時点で粉砕を終了することにより、湿式法により製造された(1)ハイドロキシアパタイト微粒子、(2)リン酸三カルシウム微粒子及び(3)炭酸カルシウム微粒子を得た。なお、リン酸三カルシウムとしては、食品添加物(和光純薬工業株式会社)を使用し、炭酸カルシウムとしては、特級試薬(和光純薬工業株式会社)を使用した(以下同様)。
ハイドロキシアパタイト、リン酸三カルシウム、及び炭酸カルシウムを、各々20%の懸濁液になるように、200mMのクエン酸ナトリウム溶液に添加した。これをダイノーミルにて0.3mmのジルコニアビーズを用いて粉砕した。30分毎に粒度分布を測定し、ほとんど粒子径に変化が見られなかった時点で粉砕を終了した。溶液中のクエン酸ナトリウム等を除去し、乾燥して、分散剤(クエン酸ナトリウム)で表面を被覆した(1)ハイドロキシアパタイト微粒子、(2)リン酸三カルシウム微粒子及び(3)炭酸カルシウム微粒子を得た。
ハイドロキシアパタイトを、20%の懸濁液になるように、200mMのクエン酸ナトリウム溶液に添加した。これをダイノーミルにて1.0mmのジルコニアビーズを用いて30分間粉砕した。溶液中のクエン酸ナトリウム等を除去し、乾燥して、分散剤(クエン酸ナトリウム)で表面を被覆した中等度に粉砕したハイドロキシアパタイト中等度粉砕微粒子を得た。
ハイドロキシアパタイトを、20%の懸濁液になるように、200mMのクエン酸ナトリウム溶液に添加し、60分間穏やかに撹拌した。溶液中のクエン酸ナトリウム等を除去し、乾燥して、分散剤(クエン酸ナトリウム)で表面を被覆したハイドロキシアパタイト粒子を得た。
ハイドロキシアパタイトを、20%の懸濁液になるように、200mMのクエン酸ナトリウム溶液に添加した。これをダイノーミルにて0.3mmのジルコニアビーズを用いて60分間粉砕した。溶液中のピロリン酸等を除去し、乾燥して、分散剤(ピロリン酸)で表面を被覆したハイドロキシアパタイト微粒子を得た。
上記の調製方法で得た各種の被覆用粒子の粒子径をレーザー回折散乱式粒度分布測定装置(株式会社堀場製作所製)を用いて測定した。その結果を表1に示す。
上記の調製方法で得た各種の被覆用粒子の比表面積を測定した(比表面積測定装置SA3100 COULTER製)。測定は、脱ガス条件150℃、20minで窒素ガスのガス吸着法により行った。その結果を表2に示す。
[母核に用いるハイドロキシアパタイト]
攪拌下の水酸化カルシウム懸濁液に、30重量%濃度のリン酸水溶液を、Ca/P比が1.67になるまで滴下した。このようにして生成したゲル状物質を室温で1日間放置して熟成した。その後、かかるゲル状物質をガラスフィルターで濾過し、残った物質をさらに100℃の空気中で乾燥を行うことにより、母核用のハイドロキシアパタイトを得た。平均粒径は20〜30μmであった。
ハイドロキシアパタイトと、メチルセルロース4000(和光純薬工業株式会社)の粉末をほぼ等量でビーカーに移し、よく混和した後、イオン交換水を徐々に加えて、ハイドロキシアパタイトとメチルセルロースを団子状にした。これら団子状にした混合粉末がゆったりと浸かるくらいにイオン交換水を加え、超音波洗浄機で5時間処理した。処理中、メチルセルロースが徐々に膨潤して全体の容量が増加するため、イオン交換水を加えた。超音波処理後、70℃に保った恒温乾燥機でゆっくりと乾燥し、混合物を適度な大きさに砕き、これを1200℃、5時間焼成して多孔質ハイドロキシアパタイトを得た。粒子径は9.242μm、比表面積は56.1m2/gであった。
難溶性物質の粒子径を、レーザー回折散乱式粒度分布測定装置(株式会社堀場製作所製)を用いて測定した。その結果を表3に示す。
6−1.実施例用
[メカノフュージョンシステムによる難溶性物質へのカルシウム化合物微粒子の被覆]
メカノフュージョンシステムAMS−MINI−GMP(ホソカワミクロン株式会社)を用いて、難溶性物質にカルシウム化合物微粒子の被覆を行った。
メカノフュージョンシステム装置に、難溶性物質とカルシウム化合物微粒子との割合を変え、合計が90g/回となるように投入し、被覆処理を行った。被覆処理中は、なるべく装置のジャケット部の温度が20℃以下になるようにアルコールでジャケットを冷却し、また、回転負荷が2.0Aを超えないように、回転数1250〜4000rpmで、15〜60分間の被覆処理を行った。回転数4000rpmで被覆処理が行えるものについては、15分間の被覆処理を行い、回転負荷が2.0Aを超えることにより、回転数が4000rpm以下となるものについては、回転数により被覆処理時間を増やし、最も回転数が少ない1250rpmで、最長60分間の被覆処理を行った。
ハイブリダーゼーションシステムNHS−1型(株式会社奈良機械製作所)を用いて、難溶性物質にカルシウム化合物微粒子の被覆を行った。
難溶性物質とカルシウム化合物微粒子を予め混合したものを、ハイブリダイゼーションシステムに、難溶性物質とカルシウム化合物微粒子との割合を変え、合計が100g/回となるように投入し、3000rpmで5分間の被覆処理を行った。
[コーティングパンによる難溶性物質へのカルシウム化合物微粒子の被覆]
難溶性物質への被覆は、コーティングパンNO.16D型(株式会社菊水製作所)を用いて行った。また、バインダーとして、エチルセルロース(約49%エトキシ)10(和光純薬工業株式会社)を用いた。
エチルセルロースをアセトンにて1%の濃度で溶解し、これにカルシウム化合物微粒子を懸濁した。難溶性粒子をコーティングパン上で緩やかに攪拌しながら、カルシウム化合物微粒子の懸濁液を噴霧した。乾燥と噴霧を繰り返し、規定量のカルシウム化合物微粒子を難溶性粒子に被覆した。
ハイブリダーゼーションシステムNHS−1型(株式会社奈良機械製作所)を用いて、各種母核粒子に難溶性物質の被覆を行った。
難溶性物質と、上記[母核に用いるハイドロキシアパタイト]で調製したハイドロキシアパタイトとを、同重量添加して、予め混合したものを、ハイブリダイゼーションシステムに、合計100g/回を投入し、3000rpmで5分間の被覆処理を行った。
また、[母核に用いるハイドロキシアパタイト]で調製したハイドロキシアパタイトの代わりに、結晶セルロースを用いて、同様に被覆処理を行った。
難溶性物質を溶媒で溶解した溶液中に、上記[多孔質ハイドロキシアパタイト]で調製した多孔質ハイドロキシアパタイトを難溶性物質重量の20倍添加し、常温、陰圧下で溶媒が完全になくなるまで放置し、難溶性物質を多孔質ハイドロキシアパタイト粒子中に含浸させた。
ガラス製の50mLスクリューキャップ遠心管に、カルシウム化合物微粒子で被覆した難溶性物質(水溶解性改善物質)と、試験液50mLを入れ、試験開始から長さ15mmの攪拌子で攪拌を行った。スターラーの回転数は120rpmで、37±0.5℃の恒温槽内で全ての試験を行った。試験液は、蒸留水及び日本薬局方崩壊試験法第二液(pH6.8)の二種類とした。日本薬局方崩壊試験法第二液は、関東化学株式会社の10倍濃度液を蒸留水で希釈して使用した。溶解性試験に用いる水溶解性改善物質量は、各水溶解性改善物質毎に上記方法で予備試験を複数回行い、360分で溶解した水溶解性改善物質量の約2倍量とした。
1.アスピリン
被覆成分欄にコーティング方法についての記載がない実施例は、被覆成分として、「D.(1)分散剤で表面を被覆したハイドロキシアパタイト微粒子」を用いた、メカノフュージョンシステムによる被覆である。また、比較例15〜49は、難溶性物質そのもの(被覆なし)である。
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
水による溶出試験 溶出量(μg/ml)
この被覆処理物質の[360分間溶解試験後の難溶性物質の溶解量]を測定した結果、蒸留水における溶解量は、1676.2μg/mlで、崩壊試験法第二液における溶解量は、1740.2μg/mlであり、これら溶解量は、いずれもアスピリン単体の蒸留水における溶解量3110.4μg/ml、崩壊試験法第二液における溶解量6552.7μg/mlよりも低く、溶解性改善効果が認められなかった。
Claims (14)
- 難溶性物質の粒子表面をカルシウム化合物微粒子を用いて被覆する水溶解性改善物質の製造方法であって、
前記難溶性物質が、医薬品、動物用医薬品、医薬部外品、化粧料及び農薬のいずれかの有効成分となる物質又は食品添加物であり、
機械的エネルギーを加えることにより、前記難溶性物質の粒子にカルシウム化合物微粒子を貫入させて該難溶性物質の粒子表面を被覆することを特徴とする水溶解性改善物質の製造方法。 - カルシウム化合物が、リン酸カルシウム又は炭酸カルシウムであることを特徴とする請求項1記載の水溶解性改善物質の製造方法。
- リン酸カルシウムが、ハイドロキシアパタイト又はリン酸三カルシウムであることを特徴とする請求項2記載の水溶解性改善物質の製造方法。
- 難溶性物質の粒子表面の少なくとも5%以上をカルシウム化合物微粒子で被覆することを特徴とする請求項1〜3のいずれか記載の水溶解性改善物質の製造方法。
- 機械的エネルギーを加える方法が、メカニカルフュージョンによる方法であることを特徴とする請求項1〜4のいずれか記載の水溶解性改善物質の製造方法。
- 機械的エネルギーを加える方法が、ハイブリダイゼーションによる方法であることを特徴とする請求項1〜4のいずれか記載の水溶解性改善物質の製造方法。
- カルシウム化合物微粒子の平均粒子径が100μm以下であることを特徴とする請求項1〜6のいずれか記載の水溶解性改善物質の製造方法。
- カルシウム化合物微粒子の比表面積が20m2/g以上であることを特徴とする請求項1〜7のいずれか記載の水溶解性改善物質の製造方法。
- カルシウム化合物微粒子が分散剤で被覆された微粒子であることを特徴とする請求項1〜8のいずれか記載の水溶解性改善物質の製造方法。
- 分散剤が、クエン酸、クエン酸塩、ピロリン酸、コンドロイチン硫酸から選ばれた少なくとも1種であることを特徴とする請求項9記載の水溶解性改善物質の製造方法。
- 難溶性物質が、樹脂及びゴムを除く物質であることを特徴とする請求項1〜10のいずれか記載の水溶解性改善物質の製造方法。
- 請求項1〜11のいずれか記載の方法により得られたことを特徴とする水溶解性改善物質。
- 請求項12記載の水溶解性改善物質を配合したことを特徴とする医薬品、動物用医薬品、医薬部外品、化粧料、農薬又は食品。
- 水性液体組成物であることを特徴とする請求項13に記載の医薬品、動物用医薬品、医薬部外品、化粧料、農薬又は食品。
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JP5909796B2 (ja) | 2012-03-02 | 2016-04-27 | 株式会社サンギ | 難溶性物質の水溶解性改善方法 |
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