JP6085307B2 - 薬理学的に活性な成分、オピオイドアンタゴニストおよび/または嫌忌剤(aversiveagent)、ポリアルキレンオキシドおよび陰イオン性ポリマーを含むタンパーレジスタント経口医薬剤形 - Google Patents
薬理学的に活性な成分、オピオイドアンタゴニストおよび/または嫌忌剤(aversiveagent)、ポリアルキレンオキシドおよび陰イオン性ポリマーを含むタンパーレジスタント経口医薬剤形 Download PDFInfo
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- JP6085307B2 JP6085307B2 JP2014541653A JP2014541653A JP6085307B2 JP 6085307 B2 JP6085307 B2 JP 6085307B2 JP 2014541653 A JP2014541653 A JP 2014541653A JP 2014541653 A JP2014541653 A JP 2014541653A JP 6085307 B2 JP6085307 B2 JP 6085307B2
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Description
これは、所定の経路により、例えば経口的に投与された場合にバイオアベイラビリティーを有しないかまたは非常に乏しいバイオアベイラビリティーのみを有するオピオイドアンタゴニストを使用することにより達成できる。医薬剤形が、例えば成分の液体抽出および該液体抽出物の別の経路による、典型的には非経口的、例えば静脈内への投与によって不正使用される場合にのみ、オピオイドアンタゴニストは十分なバイオアベイラビリティーを有し、その結果、それがその拮抗作用を展開させ、オピオイドアゴニストの悪用を回避できる。
− 医薬剤形が不正使用されず、所定の経口経路によって投与されると、特に、オピオイドアンタゴニストは好ましくは、経口投与された場合に非常に生物学的利用可能性が乏しいかまたは生物学的に利用可能でないので、オピオイドアゴニストはその所望の薬理学的効果を発現し、同時に放出されるオピオイドアンタゴニストはオピオイドアゴニストのこの効果を抑止しない。それにもかかわらず、腸では、経口投与されたオピオイドアンタゴニストが局所的にオピオイド受容体を遮断し、それによって便秘(さもなければオピオイドアゴニストによる誘導によって生じる望ましくない有害事象)を防ぐ;
− 医薬剤形が活性成分の液体抽出により不正使用され、その後規定されていない非経口経路により投与されると、オピオイドアンタゴニストは十分に生物学的に利用可能であり、従って十分にその拮抗作用を発現して、それによって、オピオイドアゴニストの悪用が回避される;
− 特に、例えば経鼻投与に好適な粉末を調製するために、乱用者にとって通常利用可能な慣用的な手段によって医薬剤形を機械的に崩壊させる試みがなされた場合、そのような試みは、医薬剤形の増加した破壊強度のために失敗する。
− 医薬剤形が不正使用されず、所定の経口経路によって投与されると、薬理学的に活性な成分、好ましくは、オピオイドアゴニストはその所望の薬理効果を発現し、嫌忌剤は薬理学的に活性な成分、好ましくはオピオイドアゴニストのこの効果を抑止しない;
− 医薬剤形が活性成分の液体抽出により不正使用され、その後規定されていない非経口経路により投与されると、嫌忌剤が十分にその嫌悪効果を発現し、それによって、薬理学的に活性な成分、好ましくはオピオイドアゴニストの悪用が回避される;
− 特に、例えば経鼻投与に好適な粉末を調製するために、乱用者にとって通常利用可能な慣用的な手段によって医薬剤形を機械的に崩壊させる試みがなされた場合、そのような試みは、医薬剤形の増加した破壊強度のために失敗する。
(i)薬理学的に活性な成分;
(ii)オピオイドアンタゴニストおよび/または嫌忌剤;および
(iii)少なくとも200,000g/molの平均分子量を有するポリアルキレンオキシドを含む。
− 医薬剤形が、(a)さらに(iv)陰イオン性ポリマーを含むか(選択肢1);又は
− 医薬剤形が、(b)少なくとも3か月の40°Cでの保管安定性を有するか(選択肢2);又は
− 医薬剤形が、(a)さらに(iv)陰イオン性ポリマーを含み、そして(b)少なくとも3か月の40°Cでの保管安定性を有する(選択肢3)。
これらの状況の下では、薬理学的に活性な成分は、好ましくはオピオイドアゴニストである。医薬剤形がオピオイドアゴニストを含まない場合、該医薬剤形は、好ましくは、オピオイドアンタゴニストも含まない。
したがって、長期放出マトリックスは好ましくは親水性マトリックスである。驚くべきことに、長期放出マトリックスからの、薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびオピオイドアンタゴニストの放出が、マトリックス中への放出媒体の浸食および拡散により制御される組み合わされたメカニズムに依拠することが見出された。
これらの状況下では、薬理学的に活性な成分はオピオイドアゴニストであることができ、またはオピオイドアゴニストでないこともできる。
(a)鼻腔および/または咽頭を刺激する物質(以下では「成分(a)」とも呼ぶ)、
(b)粘度増加剤および/またはゲル化剤(以下では、「成分(b)」とも呼ぶ)、
(c)催吐薬(以下では、「成分(c)」とも呼ぶ)、
(d)色素(以下では、「成分(d)」とも呼ぶ)、
(e)苦味物質(以下では、「成分(e)」とも呼ぶ)、
(f)界面活性剤(以下では、「成分(f)」とも呼ぶ)、
および、(a)+(b)、(a)+(c)、(a)+(d)、(a)+(e)、(a)+(f);(b)+(c)、(b)+(d)、(b)+(e)、(b)+(f);(c)+(d)、(c)+(e)、(c)+(f);(d)+(e)、(d)+(f);および(e)+(f)を含む、上記のいずれかの組み合わせ。
(a)+(c)+(d),(a)+(c)+(e),(a)+(c)+(f);
(a)+(d)+(e),(a)+(d)+(f);(a)+(e)+(f);
(b)+(c)+(d),(b)+(c)+(e),(b)+(c)+(f);
(b)+(d)+(e),(b)+(d)+(f);(b)+(e)+(f);
(c)+(d)+(e),(c)+(d)+(f);(c)+(e)+(f);
(d)+(e)+(f)。
オピオイドアゴニストが粘膜を経て、例えば経鼻的に乱用される場合、界面活性剤は嫌忌剤として機能でき、それは不快な灼熱感をもたらすことが見出された。
− 少なくとも2つの重合可能な二重結合、例えば、エチレン性不飽和官能基を有する化合物;
− 少なくとも1つの重合可能な二重結合、例えば、エチレン性不飽和官能基と、陰イオン性ポリマーの1つまたは2つ以上の繰り返し単位の別の官能基と反応できる少なくとも1つの官能基とを有する化合物;
− 陰イオン性ポリマーの1つまたは2つ以上の繰り返し単位の他の官能基と反応できる少なくとも2つの官能基を有する化合物;および
− イオン性架橋結合を、例えばアニオン性官能基によって形成できる多価金属化合物。
(vi)ポリカルボン酸のジアリルエステル又はポリアリルエステル、例えば、ジアリルフタレート、ジアリルアジペートなど;(vii)不飽和モノ又はポリカルボン酸とポリオールのモノアリルエステルとのエステル、例えば、ポリエチレングリコールモノアリルエーテルのアクリル酸エステル;および(viii)ジアリルアミン又はトリアリルアミン。
別の好ましい実施形態では、医薬剤形は、200±75mg、より好ましくは200±50mg、最も好ましくは200±25mgの範囲内の全重量を有する。別の好ましい実施形態では、医薬剤形は、250±75mg、より好ましくは250±50mg、最も好ましくは250±25mgの範囲内の全重量を有する。さらに別の好ましい実施形態では、医薬剤形は、300±75mg、より好ましくは300±50mg、最も好ましくは300±25mgの範囲内の全重量を有する。さらに別の好ましい実施形態では、医薬剤形は、400±75mg、より好ましくは400±50mg、最も好ましくは400±25mgの範囲内の全重量を有する。
好ましい実施形態では、薬理学的に活性な成分、好ましくはオピオイドアゴニストの含有量は、医薬剤形の全重量を基準として、7±6重量%、より好ましくは7±5重量%、さらに好ましくは5±4重量%、7±4重量%または9±4重量%、最も好ましくは5±3重量%、7±3重量%または9±3重量%、特に、5±2重量%、7±2重量%または9±2重量%の範囲内にある。別の好ましい実施形態において、薬理学的に活性な成分、好ましくはオピオイドアゴニストの含有量は、医薬剤形の全重量を基準として、11±10重量%、より好ましくは11±9重量%、さらにより好ましくは9±6重量%、11±6重量%、13±6重量%又は15±6重量%、最も好ましくは11±4重量%、13±4重量%又は15±4重量%、特に11±2重量%、13±2重量%又は15±2重量%の範囲内にある。さらなる好ましい実施形態では、薬理学的に活性な成分、好ましくはオピオイドアゴニストの含有量は、医薬剤形の全重量を基準として、20±6重量%、より好ましくは20±5重量%、より一層好ましくは20±4重量%、最も好ましくは20±3重量%、特に20±2重量%の範囲内にある。
この実施形態では、オピオイドアゴニストは、好ましくは、5〜80mg、好ましくは5mg、10mg、20mgまたは40mgの量で、医薬剤形に含まれる。別の特に好ましい実施形態において、オピオイドアゴニストは、オキシコドン、好ましくはそのHCl塩であり、医薬剤形は1日1回の投与に適合されている。この実施形態において、オピオイドアゴニストは好ましくは、医薬剤形中に10〜320mgの量で含有される。
これらの状況下で、オピオイドアンタゴニストは、好ましくは、その拮抗効果を発現し、それによりオピオイドアゴニストの悪用を回避させる。他方では、オピオイドアンタゴニストの目的は、好ましくは、望ましくない有害事象を減少させること、特にさもなければオピオイドアゴニストによって誘発されるであろう便秘を抑止することである。これは、医薬剤形の規定された経口投与時に、腸におけるオピオイド受容体でオピオイドアゴニストの薬理学的効果を局所的に遮断することによって達成される。
各判定前に錠剤の断片が全て除去されているよう注意して、10個の錠剤について測定を実施する。結果は、測定した力の平均値、最小値及び最大値として、全てニュートンで表す。
(i)周囲温度で30mLの精製水において30分間、本発明の元もままの医薬剤形を撹拌し;
(ii)オーバーヘッド溶液を残りから、例えば、シガレットフィルターおよびカニューレを備えたシリンジ(0.80×40mm BL/LB;21Gx 1 1/2’’)により、分離し、そして
(iii)HPLC分析によって得られた液体における薬理学的に活性な化合物の含有量を測定した場合に;
オーバヘッド液における抽出された薬理学的に活性な化合物(各場合における薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびオピオイドアンタゴニスト)の含有量は、医薬剤形における薬理学的に活性な化合物の元々の全含有量(すなわち、それが抽出試験に付される前の)に対して、最大で80重量%、77.5重量%、75重量%または72.5重量%、より好ましくは最大で70重量%、67.5重量%、65重量%または62.5重量%、さらに好ましくは最大で60重量%、57.5重量%、55重量%または52.5重量%、より一層好ましくは最大で50重量%、49重量%、48重量%または47重量%、また一層好ましくは最大で46重量%、45重量%、44重量%または43重量%、最も好ましくは最大で42重量%、41重量%、40重量%または39重量%、特に最大で38重量%、37重量%、36重量%または35重量%に達する。好ましくは、抽出された薬理学的に活性な成分、好ましくはオピオイドアゴニストの量、および抽出されたオピオイドアンタゴニストの量は、互いに、3.0重量%より大きく逸脱せず、より好ましくは2.8重量%以下、さらに好ましくは2.6重量%以下、一層好ましくは2.4重量%以下、より一層好ましくは2.2重量%以下、最も好ましくは2.0重量%以下、特に1.8重量%以下であり、ここで、パーセンテージはそれぞれ、医薬剤形に元々含まれていた薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびアンタゴニストの量に対する絶対値を意味する。
(i)30mLの沸騰精製水(約100°C)中に本発明の元のままの医薬剤形を入れ、水を30分間にわたって冷却し;
(ii)失われた水(もしあれば)を補い;
(iii)所定量のオーバーヘッド溶液を残りから、例えば、およびカニューレを備えたシリンジ(0.80×40mm BL/LB;21Gx1 1/2’’)により、分離し、そして
(iv)HPLC分析によって得られた液体における薬理学的に活性な化合物の含有量を測定した場合に;
オーバヘッド液における抽出された薬理学的に活性な化合物(各場合における薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびオピオイドアンタゴニスト)の含有量は、医薬剤形における薬理学的に活性な化合物の元々の全含有量(すなわち、それが抽出試験に付される前の)に対して、最大で21.5重量%、21.0重量%、20.5重量%または20.0重量%、より好ましくは最大で19.5重量%、19.0重量%、18.5重量%または18.0重量%、さらに好ましくは最大で17.5重量%、17.0重量%、16.5重量%または16.0重量%、より一層好ましくは最大で15.5重量%、15.0重量%、14.5重量%または14.0重量%、また一層好ましくは最大で13.5重量%、13.0重量%、12.5重量%または12.0重量%、最も好ましくは最大で11.5重量%、11.0重量%、10.5重量%または10.0重量%、特に最大で9.5重量%、9.0重量%、8.5重量%または8.0重量%に達する。好ましくは、抽出された薬理学的に活性な成分、好ましくはオピオイドアゴニストの量、および抽出されたオピオイドアンタゴニストの量は、互いに、3.0重量%より大きく逸脱せず、より好ましくは2.8重量%以下、さらに好ましくは2.6重量%以下、一層好ましくは2.4重量%以下、より一層好ましくは2.2重量%以下、最も好ましくは2.0重量%以下、特に1.8重量%以下であり、ここで、パーセンテージはそれぞれ、医薬剤形に元々含まれていた薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびアンタゴニストの量に対する絶対値を意味する。
(i)30mLの水性エタノール(40%(v/v))(周囲温度)において30分間、本発明の元のままの医薬剤形を撹拌し;
(ii)オーバーヘッド溶液を残りから、例えば、シガレットフィルターおよびカニューレを備えたシリンジ(0.80×40mm BL/LB;21Gx 1 1/2’’)により、分離し、そして
(iii)HPLC分析によって得られた液体における薬理学的に活性な化合物の含有量を測定した場合に;
オーバヘッド液における抽出された薬理学的に活性な化合物(各場合における薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびオピオイドアンタゴニスト)の含有量は、医薬剤形における薬理学的に活性な化合物の元々の全含有量(すなわち、それが抽出試験に付される前の)に対して、最大で18.5重量%、18.0重量%、17.5重量%または17.0重量%、より好ましくは最大で16.5重量%、16.0重量%、15.5重量%または15.0重量%、さらに好ましくは最大で14.5重量%、14.0重量%、13.5重量%または13.0重量%、より一層好ましくは最大で12.5重量%、12.0重量%、11.5重量%または11.0重量%、また一層好ましくは最大で10.5重量%、10.0重量%、9.5重量%または9.0重量%、最も好ましくは最大で8.5重量%、8.0重量%、7.5重量%または7.0重量%、特に最大で6.5重量%、6.0重量%、5.5重量%または5.0重量%に達する。好ましくは、抽出された薬理学的に活性な成分、好ましくはオピオイドアゴニストの量、および抽出されたオピオイドアンタゴニストの量は、互いに、3.0重量%より大きく逸脱せず、より好ましくは2.8重量%以下、さらに好ましくは2.6重量%以下、一層好ましくは2.4重量%以下、より一層好ましくは2.2重量%以下、最も好ましくは2.0重量%以下、特に1.8重量%以下であり、ここで、パーセンテージはそれぞれ、医薬剤形に元々含まれていた薬理学的に活性な成分、好ましくはオピオイドアゴニスト、およびアンタゴニストの量に対する絶対値を意味する。
− 少なくとも400N、より好ましくは少なくとも500N、さらに好ましくは少なくとも750N、より一層好ましくは少なくとも1000N、最も好ましくは少なくとも1500Nの破壊強度を有し;および/または
− オキシコドンおよびその生理学的に許容可能な塩から選択されるオピオイドアゴニストを含み;および/または
− ナロキソンおよびその生理学的に許容可能な塩から選択されるオピオイドアンタゴニスト、および/または嫌忌剤を含み;および/または
− 1日2回の経口投与用に構成され;および/または
− 医薬剤形の全重量に対して、少なくとも30重量%、より好ましくは少なくとも35重量%、さらに好ましくは少なくとも40重量%の、少なくとも500,000g/mol、より好ましくは少なくとも1,000,000g/molの平均分子量を有するポリアルキレンオキシドを含み;および/または
− 陰イオン性ポリマーとして、場合により架橋されたアクリル酸のホモ−もしくはコポリマーを含有し;および/または
− 可塑剤、好ましくはポリエチレングリコールを含み;および/または
− 酸化防止剤、好ましくはα−トコフェロールを含み;および/または
− 場合により、遊離酸、好ましくはクエン酸を含み;および/または
− 場合により、追加的なマトリックスポリマー、好ましくはセルロースエーテル、より好ましくはHPMCを含む。
a)全ての成分を混合すること;
b)場合により、工程(a)から得られた混合物を、好ましくは熱及び/又は力を工程(a)から得られた混合物に適用することによって、予備成形すること、ここで、供給される熱の量は、好ましくは、ポリアルキレンオキシドをその軟化点まで加熱するのに十分ではない;
c)熱及び力を適用することによって混合物を硬化させること、ここで、力を適用する間及び/又は力を適用する前に熱を供給することが可能であり、供給される熱の量は、ポリアルキレンオキシドを少なくともその軟化点まで加熱するのに十分なものである;
d)場合により、硬化した混合物を単体化すること;
e)場合により、医薬剤形を形作ること;および
f)場合により、フィルムコーティングを施すこと。
a)全成分を混合すること、
b)得られた混合物を押出機中で、少なくともポリアルキレンオキシドの軟化点まで加熱し、力を適用することによって押出機の出口オリフィスを通して押出すること、
c)さらに可塑性の押出物を単体化し、医薬剤形の形態にすること、又は
d)冷却され且つ任意選択で再加熱された単一化押出物を医薬剤形の形態にすること。
ミキサーは、例えば、ロールミキサー、シェーキングミキサー、剪断ミキサー又は強制的なミキサーであることができる。
ポリエチレンオキシド、α−トコフェロール、オキシコドン塩酸塩、ナロキソン塩酸塩及び全ての他の賦形剤を互いに秤量し、篩にかけた。
測定の間に、剤形が破砕されてバラバラになったか否かに関わらず、力が測定中に観察された最大の力の25%の閾値未満に減少した場合に、錠剤は破壊強度試験に不合格であるとみなした。全ての値は、10回の測定の平均として与えられる。
製剤の組成
以下の組成物を調製し、ホットメルト押出した:
錠剤をそれぞれ、円形のパンチおよび楕円形のパンチにより粗押出物から製造した(刻印なし)。以下のフォーマットを有する錠剤を、対応するパンチにより、切断した押出物から調製した:
図1Aは、組成物C−1から製造された場合の錠剤C−17 円形、C−17 両凸およびC−15 楕円形(異なる錠剤フォーマット)からのオキシコドンの、市販のTargin(登録商標)錠と比較したin vitro放出プロファイルを示す。
オキシコドン、ナロキソンおよびα−トコフェロールの含有量を欧州薬局方に従って分析的に定量し、錠剤の破壊強度を測定した。結果を、ここで下記表に要約する。
a) 剤形を鼻経路により投与可能にするための不正使用
コーヒー挽き 粉状化
ハンマーストローク 粉状化、脆性破壊
破壊強度 粉状化
振幅は1.5mmに設定した。
落下高さ:1000mm±1%
落下重量:500g±2%
落下重量/衝撃領域の形態:25mm x 25mm
サンプルの位置:サンプルホルダーの中央に緩く配置した
(A)錠剤は外観上損傷を受けていない
(B)錠剤は圧縮されたが、広く損傷を受けていない
(C)錠剤は圧縮されており、その端が傷ついている
(D)錠剤はいくつかの部分に崩壊した
(E)錠剤は粉状化された
5mLの水で5分間煮沸(元のままの錠剤、すり砕いた錠剤);フィルターおよび大きい(G21)針を用いて作成
(i)5.0mLの沸騰水に錠剤を5分間付す、
(ii)失われた水(もしあれば)を補う、
(iii)オーバーヘッド溶液を残りから、シガレットフィルターおよびカニューレを備えたシリンジ(0.80×40mm BL/LB;21Gx1 1/2’’)により、分離する、そして
(iv)HPLC分析によって得られた液体における薬理学的に活性な化合物の含有量を測定する。
30 mLの水または40%エタノールを用いた30分間の抽出
30 mLの沸騰水(茶)での30分間の抽出[水は最初に沸騰させ、次いで30分の間冷却する]
剤形C−15 楕円形、C−25 楕円形およびI−15 楕円形の保管安定性を調べた。
製剤の組成
10mmの直径、8mmの曲率半径および333.0mgの質量を有する円形の錠剤を、下記成分の混合物から調製した:
Claims (12)
- 少なくとも300Nの破壊強度を有し、そして
(i)オキシコドンまたはその生理学的に許容可能な塩;
(ii)ナロキソンまたはその生理学的に許容可能な塩;
(iii)少なくとも200,000g/molの平均分子量を有するポリアルキレンオキシド;および
(iv)次の陰イオン性ポリマー:
場合により架橋された、アクリル酸のホモポリマー;
場合により架橋された、アクリル酸とC 10 〜C 30 アルキルアクリレートとのコポリマー;あるいは
場合により架橋された、アクリル酸のホモポリマー、または場合により架橋された、アクリル酸とC 10 〜C 30 アルキルアクリレートとのコポリマー ―これらのいずれのポリマーもポリエチレングリコールとC 8 〜C 30 アルキル酸のブロックコポリマーを含有する―
を含む、保管安定な、経口投与医薬製剤。 - 欧州薬局方に従って、オキシコドンまたはその生理学的に許容可能な塩のin vitro放出プロファイルが、ナロキソンまたはその生理学的に許容可能な塩のin vitro放出プロファイルと本質的に一致する、請求項1に記載の医薬製剤。
- オキシコドンまたはその生理学的に許容可能な塩およびナロキソンまたはその生理学的に許容可能な塩が、医薬製剤にわたって、または、医薬製剤がフィルムコーティングを含む場合には医薬製剤のコーティングされたコアにわたって均一に分布する、請求項1または2に記載の医薬製剤。
- オキシコドンまたはその生理学的に許容可能な塩およびナロキソンまたはその生理学的に許容可能な塩が、ポリアルキレンオキシドおよび陰イオン性ポリマーを含む長期放出マトリックスに埋め込まれている、請求項1〜3のいずれか1つに記載の医薬製剤。
- ナロキソンに加えて、更に嫌忌剤を含むことができる、請求項1〜4のいずれか1つに記載の医薬製剤。
- 1日1回または1日2回の投与用に構成されている、請求項1〜5のいずれか1つに記載の医薬製剤。
- モノリシックである、請求項1〜6のいずれか1つに記載の医薬製剤。
- 各場合において医薬製剤の全重量を基準として、ポリアルキレンオキシドの含有量が少なくとも30重量%であり、および/または陰イオン性ポリマーの含有量が5.0±4.5重量%の範囲内である、請求項1〜7のいずれか1つに記載の医薬製剤。
- 熱成形されている、請求項1〜8のいずれか1つに記載の医薬製剤。
- ホットメルト押出されている、請求項9に記載の医薬製剤。
- タンパーレジスタントである、請求項1〜10のいずれか1つに記載の医薬製剤。
- 可塑剤および/または酸化防止剤を含む、請求項1〜11のいずれか1つに記載の医薬製剤。
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EP11009129 | 2011-11-17 | ||
EP12001295 | 2012-02-28 | ||
EP12001295.0 | 2012-02-28 | ||
PCT/EP2012/072678 WO2013072395A1 (en) | 2011-11-17 | 2012-11-15 | Tamper-resistant oral pharmaceutical dosage form comprising a pharmacologically active ingredient, an opioid antagonist and/or aversive agent, polyalkylene oxide and anionic polymer |
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JP2014533668A JP2014533668A (ja) | 2014-12-15 |
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JP2014541653A Expired - Fee Related JP6085307B2 (ja) | 2011-11-17 | 2012-11-15 | 薬理学的に活性な成分、オピオイドアンタゴニストおよび/または嫌忌剤(aversiveagent)、ポリアルキレンオキシドおよび陰イオン性ポリマーを含むタンパーレジスタント経口医薬剤形 |
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US (1) | US20130129826A1 (ja) |
EP (1) | EP2780000B1 (ja) |
JP (1) | JP6085307B2 (ja) |
KR (1) | KR20140096062A (ja) |
CN (1) | CN104066426A (ja) |
AR (1) | AR088875A1 (ja) |
AU (1) | AU2012338872B2 (ja) |
BR (1) | BR112014011504A2 (ja) |
CA (1) | CA2855718A1 (ja) |
CL (1) | CL2014000904A1 (ja) |
CO (1) | CO7210299A2 (ja) |
EA (1) | EA201400590A1 (ja) |
HK (1) | HK1200742A1 (ja) |
IL (1) | IL232054A0 (ja) |
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2012
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- 2012-11-15 EA EA201400590A patent/EA201400590A1/ru unknown
- 2012-11-15 EP EP12787711.6A patent/EP2780000B1/en not_active Not-in-force
- 2012-11-15 CA CA2855718A patent/CA2855718A1/en not_active Abandoned
- 2012-11-15 US US13/677,446 patent/US20130129826A1/en not_active Abandoned
- 2012-11-15 MX MX2014005820A patent/MX349725B/es active IP Right Grant
- 2012-11-15 BR BR112014011504A patent/BR112014011504A2/pt not_active IP Right Cessation
- 2012-11-15 CN CN201280056414.5A patent/CN104066426A/zh active Pending
- 2012-11-15 WO PCT/EP2012/072678 patent/WO2013072395A1/en active Application Filing
- 2012-11-15 AU AU2012338872A patent/AU2012338872B2/en not_active Ceased
- 2012-11-15 PE PE2014000627A patent/PE20141671A1/es not_active Application Discontinuation
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- 2012-11-15 JP JP2014541653A patent/JP6085307B2/ja not_active Expired - Fee Related
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2014
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Also Published As
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NZ623291A (en) | 2016-01-29 |
EA201400590A1 (ru) | 2014-11-28 |
US20130129826A1 (en) | 2013-05-23 |
EP2780000B1 (en) | 2019-04-03 |
CL2014000904A1 (es) | 2014-08-18 |
CN104066426A (zh) | 2014-09-24 |
AU2012338872B2 (en) | 2017-06-22 |
MX2014005820A (es) | 2014-06-04 |
JP2014533668A (ja) | 2014-12-15 |
PE20141671A1 (es) | 2014-11-22 |
AU2012338872A1 (en) | 2014-04-17 |
KR20140096062A (ko) | 2014-08-04 |
MX349725B (es) | 2017-08-10 |
HK1200742A1 (en) | 2015-08-14 |
CO7210299A2 (es) | 2015-03-09 |
AR088875A1 (es) | 2014-07-16 |
IL232054A0 (en) | 2014-05-28 |
EP2780000A1 (en) | 2014-09-24 |
BR112014011504A2 (pt) | 2017-05-09 |
WO2013072395A1 (en) | 2013-05-23 |
CA2855718A1 (en) | 2013-05-23 |
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