JP2011504902A - ロチゴチンの多形体 - Google Patents
ロチゴチンの多形体 Download PDFInfo
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- JP2011504902A JP2011504902A JP2010535352A JP2010535352A JP2011504902A JP 2011504902 A JP2011504902 A JP 2011504902A JP 2010535352 A JP2010535352 A JP 2010535352A JP 2010535352 A JP2010535352 A JP 2010535352A JP 2011504902 A JP2011504902 A JP 2011504902A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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Abstract
Description
エルゴリン化合物と対照的に、ロチゴチンは、5HT2B受容体に対して非常に低いアフィニティしか有しておらず、かくして、線維症を誘発するリスクが低い。
上記した刊行物は、各々出典明示により本明細書に組み入れる。
Cu−Kα照射(1.54060Å)で測定された下記°2θアングル(±0.2):12.04、13.68、17.72および/または19.01での少なくとも1つのピークを含むX線粉末回折スペクトル;
下記波数(±3cm−1):226.2、297.0、363.9、737.3、847.3、1018.7および/または1354.3cm−1での少なくとも1つのピークを含むラマンスペクトル;
10℃/分の加熱速度で測定し、97℃±2℃にTonsetを有する示差走査熱量測定(DSC)ピーク;
97℃±2℃の融点。
(i) 下記を含むテンパリングによるロチゴチンの新規多形体(II)の調製:
多形体(I)のロチゴチンをAlutheneバッグに入れる、
バックをシールし、38〜40℃で10日間貯蔵する;
(ii) 下記を含むエタノールスラリーからのロチゴチンの新規多形体(II)の調製:
多形体(I)のロチゴチンをエタノール中にスラリー化する、
50〜150rpmで2時間撹拌する、
所望により、多形体(I)のロチゴチンのエタノールスラリーに、多形体(II)のロチゴチンを混ぜ合わせる、
さらに、50〜150rpm、室温にて24時間撹拌する、
スラリーを濾過する、
多形体(II)のロチゴチンを重量が一定になるまで乾燥する。
調製例1
ロチゴチンの多形体(I)の試料(バッチ16208652)を、小さなAluthene(登録商標)バッグ(2006製造 Bischoff+Klein)に入れた。試料をシールし、38〜40℃で10日間貯蔵した。このインキュベーション期間の後、1gの試料を2gのEtOH中に溶解するとすぐに、形態IIの沈殿が生じた。
5.277kgのロチゴチンの多形体(I)(バッチSPM5904)を、20Lプラスチックボトルに充填し、5.3LのEtOHでエタノールスラリーとした。スラリーを窒素フラッシュした反応器に移し、プラスチックボトルをさらに8.1LのEtOHで洗浄した。洗浄液を反応器に移し、得られた懸濁液を、75rpm、室温で、24時間撹拌した。ついで、結晶スラリーを反応器からガラス吸引フィルターを介して取り出した。ついで、反応器を2.6LのEtOHで洗浄し、ついで、洗浄液を用いて得られた濾液を洗浄した。最後に、濾液を4つの重さを量った金属シートに移し、43時間40℃で重量が一定になるまで乾燥した。
単結晶X線回折
回折に適した単結晶を、ロチゴチン多形体(II)(リファレンスバッチ7769396)のメタノール溶液を急速に蒸発させることにより得た。単結晶X線回折データ(OXFORD Gemini R Ultra,Mo−Kα照射(0.71073Å))は以下の通りである:C19H25NOS,M=315.46,斜方晶系P212121,a=8.4310(10)Å,b=13.620(2)Å,c=14.868(2)Å,α=β=γ90°,V[Å3]=1707.3,Z=4,Dc[g/cm3]=1.227,λ=1.54178Å。最終的な相違因子Rは4%である。
X線分析を、Cu−Kα照射(1.54060Å)を備えたSTOE STADI−P粉末回折システムで行い、これは、ロチゴチンの多形体(II)の実験パターンが、シミュレートした粉末パターンと完全に一致することを示した。
ロチゴチンの試料をカバーガラスに置き、ついで、ただ1つの結晶に基づいて、試料を10xおよび50x-WDでフォーカライズした:Raman HJY ARAMIS,レーザー784.9nm,4x20秒,obj.10X+50X−WD,ホール 500μm,スリット100μm。4x20秒、50x−WDで取得した。
多形体(I)(バッチ1608726)および多形体(II)(バッチ7769396)のロチゴチンの熱挙動試験を、Mettler Toledo DSCシステムおよびTA Instrument(Q−1000)で行った。分析は、10℃/分の加熱速度で、30℃〜140℃の範囲の温度での貫通アルミニウムるつぼにおいて行った。
Claims (15)
- ロチゴチン((−)−5,6,7,8−テトラヒドロ−6−[プロピル−[2−(2−チエニル)エチル]−アミノ]−1−ナフタレノール)の多形体(II)。
- 下記°2θアングル(±0.2):12.04、13.68、17.72、19.01での少なくとも1つのピークを含むX線粉末回折スペクトル;
下記波数(±3cm−1):226.2、297.0、363.9、737.3、847.3、1018.7、1354.3cm−1での少なくとも1つのピークを含むラマンスペクトル;
10℃/分の加熱速度で測定し、97℃±2℃にTonsetを有するDSCピーク;
97℃±2℃の融点;
の少なくとも1つを有するロチゴチンの多形体。 - 下記X線粉末回折ピーク(°2θ)(±0.2):12.04、13.68、17.72、19.01の2、3または4つにより特徴付けられる、請求項2記載のロチゴチンの多形体。
- 実質的に図1に示されるX線粉末回折スペクトルを有するロチゴチンの多形体。
- 少なくとも5%、より好ましくは少なくとも10%の請求項1〜4いずれか1項記載のロチゴチンの多形体を含むロチゴチン原薬。
- 少なくとも50%、より好ましくは少なくとも90%の請求項1〜4いずれか1項記載のロチゴチンの多形体を含むロチゴチン原薬。
- 実質的にすべてのロチゴチンが請求項1〜4いずれか1項記載の多形体であるロチゴチン原薬。
- 治療活性物質として用いるための請求項1〜7いずれか1項記載の結晶多形。
- 請求項5〜7いずれか1項記載のロチゴチン原薬および少なくとも1つ医薬上許容される賦形剤を含む医薬組成物。
- ロチゴチン原薬が、少なくとも5%の請求項1〜4いずれか1項記載のロチゴチンの多形体を含む、請求項9記載の医薬組成物。
- 経皮治療システムの形態である、請求項9または10記載の医薬組成物。
- D2受容体アゴニストでの治療に感受的な疾患を患っている患者の治療において用いるための、請求項1〜4いずれか1項記載のロチゴチンの多形体。
- パーキンソン病、パーキンソンプラス症候群、うつ病、線維筋痛およびレストレスレッグス症候群から選択される、D2受容体アゴニストでの治療に感受的な疾患を患っている患者の治療において用いるための、請求項1〜4いずれか1項記載のロチゴチンの多形体。
- D2受容体アゴニストでの治療に感受的な疾患を患っている患者の治療用の医薬の製造における、請求項1〜4いずれか1項記載のロチゴチンの多形体の使用。
- D2受容体アゴニストでの治療に感受的な疾患が、パーキンソン病、パーキンソンプラス症候群、うつ病、線維筋痛およびレストレスレッグス症候群から選択される、請求項13記載の使用。
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99072107P | 2007-11-28 | 2007-11-28 | |
US60/990,721 | 2007-11-28 | ||
EP07121795 | 2007-11-28 | ||
EP07121795.4 | 2007-11-28 | ||
EP08166576.2 | 2008-10-14 | ||
EP08166576 | 2008-10-14 | ||
PCT/EP2008/066137 WO2009068520A2 (en) | 2007-11-28 | 2008-11-25 | Polymorphic form of rotigotine |
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JP2011504902A true JP2011504902A (ja) | 2011-02-17 |
JP5391204B2 JP5391204B2 (ja) | 2014-01-15 |
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JP2010535352A Active JP5391204B2 (ja) | 2007-11-28 | 2008-11-25 | ロチゴチンの多形体 |
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US (2) | US8592477B2 (ja) |
EP (1) | EP2215072B1 (ja) |
JP (1) | JP5391204B2 (ja) |
KR (1) | KR101694551B1 (ja) |
CN (1) | CN101970422B (ja) |
AR (1) | AR070036A1 (ja) |
AU (1) | AU2008328920B2 (ja) |
CA (1) | CA2703561C (ja) |
DK (1) | DK2215072T3 (ja) |
EA (1) | EA017836B1 (ja) |
ES (1) | ES2547231T3 (ja) |
HK (1) | HK1143162A1 (ja) |
HR (1) | HRP20150956T1 (ja) |
HU (1) | HUE027647T2 (ja) |
IL (1) | IL204991A (ja) |
ME (1) | ME02275B (ja) |
MX (1) | MX2010005925A (ja) |
MY (1) | MY165575A (ja) |
NZ (1) | NZ584363A (ja) |
PH (1) | PH12013501503A1 (ja) |
PL (1) | PL2215072T3 (ja) |
PT (1) | PT2215072E (ja) |
RS (1) | RS54235B1 (ja) |
SG (1) | SG10201610626PA (ja) |
SI (1) | SI2215072T1 (ja) |
TW (1) | TWI418349B (ja) |
WO (1) | WO2009068520A2 (ja) |
ZA (1) | ZA201002192B (ja) |
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JP2016500086A (ja) * | 2012-11-22 | 2016-01-07 | ウーツェーベー ファルマ ゲーエムベーハーUcb Pharma Gmbh | ロチゴチンの経皮投与のための複数日用のパッチ |
US9737548B2 (en) | 2005-11-11 | 2017-08-22 | Eb Ip Lybrido B.V. | Pharmaceutical formulations and uses thereof in the treatment of female sexual dysfunction |
US10314848B2 (en) | 2006-11-03 | 2019-06-11 | Eb Ip Lybridos B.V. | Use of testosterone and a 5-HT1A agonist in the treatment of sexual dysfunction |
WO2019124261A1 (ja) | 2017-12-19 | 2019-06-27 | 久光製薬株式会社 | ロチゴチン含有貼付剤 |
US10441592B2 (en) | 2004-05-11 | 2019-10-15 | Eb Ip Lybrido B.V. | Pharmaceutical formulations and uses thereof in the treatment of female sexual dysfunction |
WO2020166298A1 (ja) | 2019-02-15 | 2020-08-20 | 久光製薬株式会社 | ロチゴチン安定化方法 |
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US11426359B2 (en) | 2014-05-20 | 2022-08-30 | Lts Lohmann Therapie-Systeme Ag | Method for adjusting the release of active agent in a transdermal delivery system |
US11633367B2 (en) | 2014-05-20 | 2023-04-25 | Lts Lohmann Therapie-Systeme Ag | Transdermal delivery system containing rotigotine |
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US20030026830A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine |
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JP5391204B2 (ja) * | 2007-11-28 | 2014-01-15 | ウーツェーベー ファルマ ゲーエムベーハー | ロチゴチンの多形体 |
EP2281559A1 (en) | 2009-06-26 | 2011-02-09 | UCB Pharma GmbH | Pharmaceutical composition comprising rotigotine salts (acid or Na), especially for iontophoresis |
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KR20200074186A (ko) | 2017-12-19 | 2020-06-24 | 히사미쓰 세이야꾸 가부시키가이샤 | 로티고틴 함유 첩부제 |
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