JP2013529221A - システアミン誘導体、および非アルコール性脂肪性肝炎の治療におけるその使用 - Google Patents
システアミン誘導体、および非アルコール性脂肪性肝炎の治療におけるその使用 Download PDFInfo
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Abstract
Description
本出願は2010年6月8日に提出されたアメリカ合衆国仮特許出願番号61/352438の優先権を主張するものである。本出願はここに参照によりそのすべての開示内容に関して全体を組み込むものである。
(I)
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィドの少なくとも1つを表す
R3は、独立して、以下の少なくとも1つを表す。
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィドの少なくとも1つを表す。
R3は、独立して、以下の少なくとも1つを表す。
たとえば、
(Ia)
(Ib)
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィドの少なくとも1つを表す。
R3は、独立して、下記の少なくとも1つを表す。
例えば、
(Ia) (Ib)
の少なくとも1つを表し、R3は、独立して、下記の少なくとも1つを表す。
例えば、
(Ia)
(Ib)
(Ic)
(Id)
最終化合物
この発明にかなう適切な単位投与形態としては、錠剤、カプセル剤、トローチ剤、坐剤、粉末パケット、ウエハース、カシェ剤、茶さじ分、大匙分、スポイト分、アンプル、バイアル、また上記のいずれかの隔離された倍数、および本明細書に既述された他の形態である。
調節された放出の種類には、制御、長時間化、持続、拡張、遅延、拍動性、反復行動化されたなどが挙げられる。これらの種類の調節された放出を達成するための適切なメカニズムには、拡散、浸食、ジオメトリおよび/または不浸透性の障壁を介した表面面積制御、または当技術分野で公知の他のメカニズムを含む。
合成の方法:
(I)
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィド
の少なくとも1つを表す。R3はまた、独立して
の少なくとも1つを表す。
Claims (14)
- 次式Iの薬学的に許容される化合物を含む、化合物。
(ここで、R1、R2はそれぞれ独立に、以下の少なくとも1つを表す:水素、メチルアミン、シキヘキシルメチルエーテル、ブトキシ基、プロポキシ基、チオール、アルキル、アルキルチオール、アセチルチオール、ジスルフィド基、アシル基、アシルアルキル、アルケニル、アルキルチオアルキル、アルキニル、アリールアルコキシ、アルコキシアルキル、アラルキル、アリール、アリールチオアルキル、シクロアルキル、エーテル、エステル、ヘテロアリール、ヘテロシクリル、低級アルキル基、スルホン、スルホキシド、またはヒドロキシアルキル;
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィド
の少なくとも1つを表す。R3はまた、独立して
の少なくとも1つを表す。) - 式Iの化合物は代謝性疾患の治療のために処方される、請求項1に記載の化合物。
- 式Iの化合物は神経変性疾患の治療のために処方される、請求項1に記載の化合物。
- 式Iの化合物は、非経口投与、注射、皮下、経口液剤、経口投与及び経皮投与の少なくとも一つのために処方される、請求項2に記載の化合物。
- 経口投与は遅延放出または徐放性製剤の少なくとも一つを含む腸溶性コーティングを有する、請求項5に記載の組成物。
- 式Iの化合物の合成法であって、
水素化アルミニウムリチウムを0℃で、THF中のエイコサペンタエン酸の懸濁液としてTHF溶液中で混合する工程と、
反応混合物を室温に温める工程と、
一晩室温を維持する工程と、
前記反応混合物を飽和硫酸ナトリウムで急冷し、酢酸エチルで抽出する工程と、
有機層を分離し、ブラインで洗浄する工程と、
洗浄された層を無水Na2SO4で乾燥し、化合物2を作るために、減圧下で蒸発させる工程と、
カラムクロマトグラフィーにより化合物2を精製する工程と、
を含む合成法。 - 室温でアルコール及びピリジンのDCM溶液に4−ニトロフェニルクロロホルメートを混合する工程と、
化合物2と溶液を室温で3時間撹拌する工程と、
薄層クロマトグラフィーにより反応の終了を監視する工程と、
反応混合物をDCMで希釈する工程と、
水で洗浄し、続いてNaHCO3溶液で洗浄する工程と、
無水Na2SO4で反応混合物を乾燥し、減圧下で蒸発させて固体を形成する工程と、
酢酸エチル8%で固形物を精製および溶出し、溶離剤として化合物3として無色の液体を得る工程と、
溶離液として8パーセント酢酸エチル−ペットのエーテルを使用して100〜200メッシュのシリカゲルのカラムクロマトグラフィーで溶離液を精製し化合物3を得る工程と、
をさらに含む、請求項7に記載の方法。 - 2−アミノエタンチオール塩酸のTFA溶液にトリチルアルコールを0℃で添加する工程と、
室温で3時間反応混合物を撹拌する工程と、
反応混合物を、飽和NaHCO3溶液で急冷し、EtOACで抽出する工程と、
水(2×100mL)で洗浄し、次にブライン溶液で洗浄する工程と、
無水Na2SO4上で乾燥させ、減圧下で蒸発させて粘稠な油としての粗生成物を得る工程と、
シリカゲル60〜120メッシュと、溶離液としてクロロホルム中の5%MeO上で、カラムクロマトグラフィーを用いて精製し、溶出し、化合物3をトリチル保護された白色固体として得る工程と、をさらに含む、請求項8に記載の方法。 - 室温で乾燥DMF中の炭酸塩の溶液に化合物3を加える工程と、
室温で2時間、反応混合物を保持する工程と、
減圧下で反応混合物を蒸発させる工程と、
この反応混合物を60〜120メッシュのシリカゲル上でカラムクロマトグラフィー使用し、14%酢酸エチル−ペットのエーテルを加えて精製、溶出し、化合物4を無色液体として得る工程と、
をさらに含む、請求項9に記載の方法。 - 炭酸塩の20%TFA/DCM溶液とトリエチルシランを0℃で滴下により添加する工程と、
0℃で30分間反応混合物を撹拌する工程と、
薄層クロマトグラフィーを用いて反応の終了を監視する工程と、
この反応混合物と飽和NaHCO3溶液を混合し、DCMで抽出する工程と、
前記反応混合物を一緒にした有機層をブライン溶液で洗浄する工程と、
無水Na2SO4上で反応混合物を乾燥させ、減圧下で蒸発させる工程と、
溶離剤として酢酸エチル−ペットエチルエーテル15%を使用し、60〜120メッシュのシリカゲル上でカラムクロマトグラフィーを用いて精製し、最終化合物を無色の液体として得る工程と、
を含む、請求項10に記載の方法。 - 次式Iの薬学的に許容される化合物を含む、次式Iの化合物の薬学的に許容される塩を含む、キット。
(ここで、R1、R2はそれぞれ独立に、下記の少なくとも1つを表す:水素、メチルアミン、シキヘキシルメチルエーテル、ブトキシ基、プロポキシ基、チオール、アルキル、アルキルチオール、アセチルチオール、ジスルフィド基、アシル基、アシルアルキル、アルケニル、アルキルチオアルキル、アルキニル、アリールアルコキシ、アルコキシアルキル、アラルキル、アリール、アリールチオアルキル、シクロアルキル、エーテル、エステル、ヘテロアリール、ヘテロシクリル、低級アルキル基、スルホン、スルホキシド、またはヒドロキシアルキル;
R2はまた、独立して、水素、カルボキシル、アミン、−NH−CO−NH−、−NH−CO−CH2−NH−、−NH−CO−、R−COO−R1、チオール、ジスルフィド
の少なくとも1つを表す。R3はまた、独立して
の少なくとも1つを表す。) - 神経変性障害および代謝性疾患の少なくとも1つを治療するにあたり使用する指示をさらに含む、請求項12記載のキット。
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US35243810P | 2010-06-08 | 2010-06-08 | |
US61/352,438 | 2010-06-08 | ||
PCT/IB2011/001550 WO2011154833A1 (en) | 2010-06-08 | 2011-06-03 | Cysteamine derivatives and their use in the treatment of nash |
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JP2013529221A true JP2013529221A (ja) | 2013-07-18 |
JP5885085B2 JP5885085B2 (ja) | 2016-03-15 |
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US (1) | US20110300190A1 (ja) |
EP (1) | EP2580204B1 (ja) |
JP (1) | JP5885085B2 (ja) |
CN (1) | CN102947287A (ja) |
AU (1) | AU2011263423B2 (ja) |
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CA (1) | CA2801336C (ja) |
IL (1) | IL223241A (ja) |
SG (1) | SG185754A1 (ja) |
WO (1) | WO2011154833A1 (ja) |
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WO1996001558A1 (en) * | 1994-07-11 | 1996-01-25 | Pate David W | Anandamide analogue compositions and method of treating intraocular hypertention using same |
WO2009070781A1 (en) * | 2007-11-30 | 2009-06-04 | The Regents Of The University Of California | Methods of treating non-alcoholic steatohepatitis (nash) using cysteamine products |
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EP2580204B1 (en) | 2017-03-08 |
WO2011154833A1 (en) | 2011-12-15 |
US20110300190A1 (en) | 2011-12-08 |
EP2580204A1 (en) | 2013-04-17 |
IL223241A (en) | 2017-12-31 |
CA2801336C (en) | 2020-01-28 |
AU2011263423A1 (en) | 2012-08-23 |
JP5885085B2 (ja) | 2016-03-15 |
IL223241A0 (en) | 2013-02-03 |
BR112012031194A2 (pt) | 2018-05-29 |
CN102947287A (zh) | 2013-02-27 |
SG185754A1 (en) | 2012-12-28 |
CA2801336A1 (en) | 2011-12-15 |
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