JP5253737B2 - D3アゴニスト性治療薬としての(s)−2−n−プロピルアミノ−5−ヒドロキシテトラリン - Google Patents
D3アゴニスト性治療薬としての(s)−2−n−プロピルアミノ−5−ヒドロキシテトラリン Download PDFInfo
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
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Description
その際R2及びR3はそれぞれ、H、C1〜6アルキル、C3〜10シクロアルキル、ベンジル又はフェニルから選択されている]のプロドラッグを含有し、
その際この式Iの化合物が純(S)−エナンチオマーとして存在する医薬品である。
1.レセプターアフィニティーの測定
レセプターアフィニティーを置き換え実験により測定した。この目的のために、前記レセプターを放射性物質により標識化し、レセプター特異的なリガンドとインキュベーションした。主に、細胞系で発現されるヒトのレセプターを使用した。又は、ラットの脳又はウシの脳からの膜調製物を使用した。このインキュベーション条件は刊行されかつ標準化されている。前記インキュベーションバッチに、試験すべき物質((S)−2−N−プロピルアミノ−5−ヒドロキシテトラリン)の様々な濃度を添加し、これにより用量−結合曲線が作成できる。非特異的な結合は、非特異的なリガンドとのインキュベーションを介して特異的な結合により分離される。特異的な結合の割合は様々な物質濃度の際に、このリガンドの最大結合の%で示される。IC50値(前記リガンドの結合の、50%の阻害の際の濃度)及び傾斜を、回帰分析を用いて算出した。Cheng−Pusoff−方程式を用いて、このKi値を算出し、前記値を次いで比較のために動員した:前記Ki値が低くなるほど、前記アフィニティーは高まる(参照、表1)。
前記物質の本来の活性を測定すべく、ヒトのドパミンレセプターを細胞系(CHO−DUKX−SRE又はSH−SY5Y−SRE)で機能的に発現させた。これは、アゴニストの結合により細胞内シグナルカスケードが活性化し、これにより更なるタンパク質の形成を生じることを意味する。このタンパク質の遺伝子に、ルシフェラーゼを前もって人為的に挿入させていた。前記タンパク質の刺激は、ルシフェラーゼの形成をも生じ、前記ルシフェラーゼはATPの存在下で光子の放出を誘導し(いわゆるルミネセンス)、これは次に測光分析により測定できる。前記ルミネッセンスの強度は、前記レセプターの刺激に比例する。ドパミンアゴニストは前記ルミネセンスを促進する一方でアンタゴニストは固有の作用を発揮しない。アンタゴニストはしかし、ドパミンにより誘発されたルミネセンス又はアゴニストにより誘発されたルミネセンスを阻害する。この活性は様々な物質濃度で、内因性のリガンド又は適したアゴニストによる最大の活性化の%で示される。このEC50値(50%の活性化の際の濃度)及び傾斜は、回帰分析を用いて算出される。Cheng−Pusoff−方程式を用いてこのKi値を算出し、前記値を次いで比較のために動員した:前記Ki値が低くなるほど、このアフィニティー及び活性は高まる。(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリンのドパミンレセプターに対する作用に関しては表2に挙げた値が見出された。
ヒト、サル、イヌ、ラット又はマウスの肝臓細胞ホモジネートから分画遠心法により、このミクロソーム分画を得、これは本質的な代謝酵素を含有する;又はこの細胞質分画をも得てよい。この細胞成分分画を緩衝液中で懸濁し、これにより定義されたタンパク質含量を有する溶液を得た。1μMのこの試験すべきプロドラッグの添加後に、37℃で60分間のインキュベーションを行った。引き続き(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリンを、HPLC/UVを用いるか又はHPLC/MSも用いて定量し、かつ使用した量と関連付けた。より詳細な分析に関しては、濃度系列又は時系列を調べた。
(a)Miglyol 812 1411.2gを、Duranフラスコ中に量り取った。Imwitor 312 14.4gを前記Miglyolに添加し、引き続き30分間撹拌下で80℃に加熱した。この澄んだ溶液を、室温にまで冷却し、濾別した。
Claims (5)
- (S)−2−N−プロピルアミノ−5−ヒドロキシテトラリン又はその医薬的に許容可能な塩又は(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリンのプロドラッグを含有するD3選択的アゴニスト剤であって、前記プロドラッグが、一般式I
その際R2及びR3はそれぞれ、H、C1〜6アルキル、C3〜10シクロアルキル、ベンジル又はフェニルから選択されている]
で示される、D3選択的アゴニスト剤。 - 一般式Iで示される、(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリンのプロドラッグ中R1はC1〜6アルキルカルボニル、C3〜10シクロアルキルカルボニル、ベンゾイル、−C(O)NR2R3及び−C(O)NHR2から選択されている、請求項1記載のD3選択的アゴニスト剤。
- うつ病、レストレスレッグ症候群、DOPA感受性ジスキネジア、パーキンソン病関連運動障害、DOPA誘発性運動障害、コカイン中毒、アルコール中毒、オピエート中毒及びニコチン中毒、神経変性疾患のグループから選択された疾病の治療又は予防のための、(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリン又はその医薬的に許容可能な塩又は(S)−2−N−プロピルアミノ−5−ヒドロキシテトラリンのプロドラッグを含有することにより特徴付けられる医薬品であって、前記プロドラッグは請求項1又は2に定義されている、医薬品。
- 前記疾病が、
(a)パーキンソン病に関連しているか、又は
(b)L−DOPA誘発性である
運動障害である、請求項3記載の医薬品。 - 経皮投与用、経粘膜投与用又は非経口投与用の、請求項3又は4記載の医薬品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10359528.7 | 2003-12-18 | ||
DE10359528A DE10359528A1 (de) | 2003-12-18 | 2003-12-18 | (S)-2-N-Propylamino-5-hydroxytetralin als D3-agonistisches Therapeutikum |
PCT/EP2004/014143 WO2005058296A1 (de) | 2003-12-18 | 2004-12-13 | (s)-2-n-propylamino-5-hydroxytetralin als d3-agonistisches therapeutikum |
Publications (3)
Publication Number | Publication Date |
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JP2007514674A JP2007514674A (ja) | 2007-06-07 |
JP2007514674A5 JP2007514674A5 (ja) | 2008-02-14 |
JP5253737B2 true JP5253737B2 (ja) | 2013-07-31 |
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JP2006544295A Expired - Fee Related JP5253737B2 (ja) | 2003-12-18 | 2004-12-13 | D3アゴニスト性治療薬としての(s)−2−n−プロピルアミノ−5−ヒドロキシテトラリン |
Country Status (22)
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US (2) | US8609641B2 (ja) |
EP (1) | EP1694318B1 (ja) |
JP (1) | JP5253737B2 (ja) |
KR (1) | KR101083568B1 (ja) |
CN (1) | CN1929829B (ja) |
AT (1) | ATE356621T1 (ja) |
AU (1) | AU2004298341B2 (ja) |
BR (1) | BRPI0417739A (ja) |
CA (1) | CA2547820C (ja) |
CY (1) | CY1106589T1 (ja) |
DE (2) | DE10359528A1 (ja) |
DK (1) | DK1694318T3 (ja) |
ES (1) | ES2282923T3 (ja) |
HK (1) | HK1094421A1 (ja) |
HR (1) | HRP20070175T3 (ja) |
IS (1) | IS2533B (ja) |
MX (1) | MXPA06006696A (ja) |
PL (1) | PL1694318T3 (ja) |
PT (1) | PT1694318E (ja) |
RS (1) | RS50536B (ja) |
SI (1) | SI1694318T1 (ja) |
WO (1) | WO2005058296A1 (ja) |
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DE10334188B4 (de) | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
DE10359528A1 (de) | 2003-12-18 | 2005-07-28 | Schwarz Pharma Ag | (S)-2-N-Propylamino-5-hydroxytetralin als D3-agonistisches Therapeutikum |
EP1547592A1 (en) | 2003-12-23 | 2005-06-29 | Schwarz Pharma Ag | Intranasal formulation of rotigotine |
DE10361258A1 (de) | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
US20050197385A1 (en) * | 2004-02-20 | 2005-09-08 | Schwarz Pharma Ag | Use of rotigotine for treatment or prevention of dopaminergic neuron loss |
DE102004014841B4 (de) * | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
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EP1987815A1 (en) * | 2007-05-04 | 2008-11-05 | Schwarz Pharma Ag | Oronasopharyngeally deliverable pharmaceutical compositions of dopamine agonists for the prevention and/or treatment of restless limb disorders |
CN101970422B (zh) * | 2007-11-28 | 2014-10-22 | Ucb制药有限公司 | 罗替高汀的多晶型物 |
US8604242B2 (en) * | 2008-10-13 | 2013-12-10 | Interquim, S.A. | Process for the preparation of optically active (S)-(−)-2-(N-propylamino)-5-methoxytetraline and (S)-(−)-2-(N-propylamino)-5-hydroxytetraline compounds |
EP2281559A1 (en) | 2009-06-26 | 2011-02-09 | UCB Pharma GmbH | Pharmaceutical composition comprising rotigotine salts (acid or Na), especially for iontophoresis |
WO2011047350A2 (en) * | 2009-10-16 | 2011-04-21 | David Helton | Emesis treatment |
ME03053B (me) | 2009-12-22 | 2018-10-20 | Ucb Biopharma Sprl | Polivinilpirolidon za stabilizaciju čvrste disperzije nekristalnog oblika rotigotina |
EP2697238B1 (en) * | 2011-04-08 | 2019-03-20 | Laurus Labs Limited | Solid forms of antiretroviral compounds, process for the preparation and their pharmaceutical composition thereof |
EP2559435A1 (en) | 2011-08-19 | 2013-02-20 | UCB Pharma GmbH | Rotigotine in the treatment of hemispatial neglect, stroke and deficits following stroke |
CN102634064B (zh) * | 2012-04-10 | 2013-09-11 | 宁波长阳科技有限公司 | 一种含磷阻燃剂、阻燃聚酯薄膜及其制备方法 |
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- 2004-12-13 RS RSP-2007/0117A patent/RS50536B/sr unknown
- 2004-12-13 WO PCT/EP2004/014143 patent/WO2005058296A1/de active Application Filing
- 2004-12-13 PT PT04803781T patent/PT1694318E/pt unknown
- 2004-12-13 AT AT04803781T patent/ATE356621T1/de active
- 2004-12-13 DE DE502004003249T patent/DE502004003249D1/de active Active
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- 2006-06-12 KR KR1020067011512A patent/KR101083568B1/ko not_active IP Right Cessation
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- 2007-02-05 HK HK07101358A patent/HK1094421A1/xx not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
---|---|
IS2533B (is) | 2009-07-15 |
IS8505A (is) | 2006-06-12 |
SI1694318T1 (sl) | 2007-08-31 |
PT1694318E (pt) | 2007-05-31 |
CN1929829B (zh) | 2010-12-15 |
US20140051768A1 (en) | 2014-02-20 |
CY1106589T1 (el) | 2012-01-25 |
EP1694318B1 (de) | 2007-03-14 |
JP2007514674A (ja) | 2007-06-07 |
DK1694318T3 (da) | 2007-06-25 |
ES2282923T3 (es) | 2007-10-16 |
PL1694318T3 (pl) | 2007-07-31 |
AU2004298341B2 (en) | 2011-03-10 |
HRP20070175T3 (en) | 2007-06-30 |
ATE356621T1 (de) | 2007-04-15 |
KR20060126500A (ko) | 2006-12-07 |
HK1094421A1 (en) | 2007-03-30 |
RS50536B (sr) | 2010-05-07 |
WO2005058296A1 (de) | 2005-06-30 |
AU2004298341A1 (en) | 2005-06-30 |
US9108900B2 (en) | 2015-08-18 |
US20070197480A1 (en) | 2007-08-23 |
DE10359528A1 (de) | 2005-07-28 |
KR101083568B1 (ko) | 2011-11-14 |
DE502004003249D1 (en) | 2007-04-26 |
US8609641B2 (en) | 2013-12-17 |
CN1929829A (zh) | 2007-03-14 |
EP1694318A1 (de) | 2006-08-30 |
CA2547820C (en) | 2013-02-19 |
MXPA06006696A (es) | 2006-08-31 |
BRPI0417739A (pt) | 2007-04-03 |
CA2547820A1 (en) | 2005-06-30 |
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