JP2014508184A5 - - Google Patents

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JP2014508184A5
JP2014508184A5 JP2013558454A JP2013558454A JP2014508184A5 JP 2014508184 A5 JP2014508184 A5 JP 2014508184A5 JP 2013558454 A JP2013558454 A JP 2013558454A JP 2013558454 A JP2013558454 A JP 2013558454A JP 2014508184 A5 JP2014508184 A5 JP 2014508184A5
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  1. 全ての互変異性体及び立体異性体を含む、式(I)の化合物、又はその医薬として許容し得る塩、溶媒和物、若しくは多形体：
    Figure 2014508184
     (式中、R1は、水素、ハロゲン、-C1-6アルキル、C2-6アルケニル、C2-6アルキニル、-アリール、-C1-6アルキルアリール、-シクロアルキル、-C1-6アルキルシクロアルキル、-ヘテロアリール、-C1-6アルキルヘテロアリール、-ヘテロシクリル、-C1-6アルキルヘテロシクリル、フェニルにより置換された-シクロアルキル、フェノキシにより置換された-シクロアルキル、シクロアルキルにより置換された-フェニル、フェノキシにより置換された-フェニル、フェニルにより置換された-フェニル、フェニルにより置換されたヘテロシクリル、フェニルにより置換されたヘテロアリール、ヘテロシクリルにより置換されたフェニル、ヘテロアリールにより置換されたフェニル、-O-シクロアルキルにより置換されたフェニル、-ヘテロシクリル-フェニルにより置換されたフェニル、又は-シクロアルキル-ヘテロシクリルにより置換されたフェニルを表し;
    前記アリール、シクロアルキル、ヘテロシクリル、ヘテロアリール、フェニル、又はフェノキシ基のいずれも、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C1-6ハロアルキル、-C1-6チオアルキル、-SOC1-4アルキル、-SO2C1-4アルキル、C1-6アルコキシ-、C1-6ハロアルコキシ、-O-C3-8シクロアルキル、C3-8シクロアルキル、-SO2C3-8シクロアルキル、-SOC3-6シクロアルキル、C3-6アルケニルオキシ-、C3-6アルキニルオキシ-、-C(O)C1-6アルキル、-C(O)OC1-6アルキル、C1-6アルコキシ-C1-6アルキル-、ニトロ、ハロゲン、シアノ、ヒドロキシル、=O、-C(O)OH、-NH2、-NHC1-4アルキル、-N(C1-4アルキル)(C1-4アルキル)、-C(O)N(C1-4アルキル)(C1-4アルキル)、-C(O)NH2、-C(O)NH(C1-4アルキル)、及び-C(O)NH(C3-10シクロアルキル)から選択される1個以上のRb基により任意に置換されていてよく;
    R2は、=O、-O-C1-6アルキル、-NR3R4、又は-O-C1-6ハロアルキルを表し;
    R3及びR4は、独立に、水素、C1-6アルキル、又はC3-8シクロアルキルを表し;或いは、R3とR4とは、それらが結合する窒素原子と共に、1個以上のRb基により任意に置換されているヘテロシクリル基を形成してよく;
    nは、0〜3から選択される整数を表し;かつ
    Raは、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C1-6ハロアルキル、-C1-6チオアルキル、-SOC1-4アルキル、-SO2C1-4アルキル、C1-6アルコキシ-、-O-C3-8シクロアルキル、C3-8シクロアルキル、-SO2C3-8シクロアルキル、-SOC3-6シクロアルキル、C3-6アルケニルオキシ-、C3-6アルキニルオキシ-、-C(O)C1-6アルキル、-C(O)OC1-6アルキル、C1-6アルコキシ-C1-6アルキル-、ニトロ、ハロゲン、シアノ、ヒドロキシル、-C(O)OH、-NH2、-NHC1-4アルキル、-N(C1-4アルキル)(C1-4アルキル)、-C(O)N(C1-4アルキル)(C1-4アルキル)、-C(O)NH2、-C(O)NH(C1-4アルキル)、及び-C(O)NH(C3-10シクロアルキル)を表す）。
  2. R1が、-C1-6アルキル、-アリール、-シクロアルキル、-ヘテロアリール、-ヘテロシクリル、フェニルにより置換された-シクロアルキル、フェノキシにより置換された-シクロアルキル、シクロアルキルにより置換された-フェニル、フェノキシにより置換された-フェニル、フェニルにより置換された-フェニル、フェニルにより置換されたヘテロシクリル、フェニルにより置換されたヘテロアリール、ヘテロシクリルにより置換されたフェニル、ヘテロアリールにより置換されたフェニル、-O-シクロアルキルにより置換されたフェニル、-ヘテロシクリル-フェニルにより置換されたフェニル、又は-シクロアルキル-ヘテロシクリルにより置換されたフェニルを表す、請求項１記載の化合物。
  3. R1が、-C1-6アルキル、-アリール、-シクロアルキル、-ヘテロアリール、フェニルにより置換された-シクロアルキル、フェノキシにより置換された-シクロアルキル、シクロアルキルにより置換された-フェニル、フェニルにより置換された-フェニル、フェニルにより置換されたヘテロシクリル、ヘテロシクリルにより置換されたフェニル、-O-シクロアルキルにより置換されたフェニル、-ヘテロシクリル-フェニルにより置換されたフェニル、又は-シクロアルキル-ヘテロシクリルにより置換されたフェニルを表す、請求項２記載の化合物。
  4. R1が、-C1-6アルキル、-アリール、-シクロアルキル、-ヘテロアリール、シクロアルキルにより置換された-フェニル、フェニルにより置換された-フェニル、ヘテロシクリルにより置換されたフェニル、-ヘテロシクリル-フェニルにより置換されたフェニル、又は-O-シクロアルキルにより置換されたフェニルを表し、式中、該フェニル基が、1個以上のハロゲン、C1-6アルコキシ、又はC1-6ハロアルコキシ基により任意に置換されており、式中、該ヘテロシクリル基が、1個以上のC1-6アルキル、ハロゲン、C3-8シクロアルキル、ヒドロキシル、又は=O基により任意に置換されており、かつ、式中、該シクロアルキル基が1個以上のハロゲン又は=O基により任意に置換されている、請求項３記載の化合物。
  5. R1が、-アリール(例えば、フェニル)、シクロアルキルにより置換された-フェニル(例えば、-フェニル-シクロヘキシル)、ヘテロシクリルにより置換されたフェニル(例えば、-フェニル-ピロリジニル、-フェニル-モルホリニル、-フェニル-チオモルホリニル、-フェニル-ピペリジニル、-フェニル-ピペラジニル、-フェニル-テトラヒドロチオピラニル、又は-フェニル-テトラヒドロピラニル)、又は-ヘテロシクリル-フェニルにより置換されたフェニル(例えば、-フェニル-ピペラジニル-フェニル)を表し;式中、該フェニル基が、1個以上のハロゲン(例えば、フッ素、臭素、又は塩素)、C1-6アルコキシ(例えば、ブトキシ)、又はC1-6ハロアルコキシ(例えば、ジフルオロブトキシ)基により任意に置換されており;式中、該ヘテロシクリル基が、1個以上のC1-6アルキル(例えば、メチル)、ハロゲン(例えば、フッ素)、C3-8シクロアルキル(例えば、シクロプロピル)、ヒドロキシル、又は=O基により任意に置換されており;かつ、式中、該シクロアルキル基が、1個以上のハロゲン(例えば、フッ素)又は=O基により任意に置換されている、請求項４記載の化合物。
  6. R1が、-フェニル-モルホリニル又は-フェニル-チオモルホリニルなどのヘテロシクリルにより置換された-フェニルを表し、式中、該ヘテロシクリル基が、1個以上の=O基により任意に置換されている、請求項４記載の化合物。
  7. R2が、=O、-O-C1-6アルキル(例えば、メトキシ)、又はNR3R4(例えば、-NHMe、-N(Me)2)、-NH-シクロヘキシル、又はピペリジニル、ピペラジニル、若しくはモルホリニルなどの複素環基を表し、式中、該複素環基が、ハロゲン(例えば、フッ素)又はC1-6アルキル(例えば、メチル)などの1個以上のRb基により任意に置換されている、請求項１〜６のいずれか一項記載の化合物。
  8. R2が、=O、メトキシなどの-O-C1-6アルキル、又はピペリジニルなどのNR3R4を表す、請求項１〜６のいずれか一項記載の化合物。
  9. nが0を表す、請求項１〜８のいずれか一項記載の化合物。
  10. 全ての互変異性体及び立体異性体を含む、実施例１〜３３のいずれか１つ記載の化合物、又はその医薬として許容し得る塩、溶媒和物、若しくは多形体。
  11. 医薬として使用するための、請求項１〜１０記載の化合物。
  12. 任意に1種以上の治療上許容し得る希釈剤又は担体と組み合わせて、請求項１〜１０のいずれか一項記載の化合物を含む、医薬組成物。
  13. 神経保護薬、抗パーキンソン病薬、アミロイドタンパク質沈着阻害剤、βアミロイド合成阻害剤、抗うつ薬、抗不安薬、抗精神病薬、及び抗多発性硬化症薬からなる群から選択される少なくとも1種の化合物をさらに含む、請求項１２記載の医薬組成物。
  14. PEP-阻害剤、LiCl、DP IV又はDP IV様酵素の阻害剤の阻害剤、アセチルコリンエステラーゼ(ACE)阻害剤、PIMTエンハンサー、βセクレターゼの阻害剤、γセクレターゼの阻害剤、中性エンドペプチダーゼの阻害剤、ホスホジエステラーゼ-4(PDE-4)の阻害剤、TNFα阻害剤、ムスカリン性M1受容体アンタゴニスト、NMDA受容体アンタゴニスト、σ-1受容体阻害剤、ヒスタミンH3アンタゴニスト、免疫調節薬、免疫抑制薬、又はアンテグレン(ナタリズマブ)、Neurelan(ファムプリジン-SR)、カンパス(アレムツズマブ)、IR 208、NBI 5788／MSP 771(チプリモチド)、パクリタキセル、Anergix.MS(AG 284)、SH636、ディフェリン(CD 271, アダパレン)、BAY 361677(インターロイキン-4)、マトリックス-メタロプロテイナーゼ-阻害剤、インターフェロン-τ(トロホブラスチン)、及びSAIK-MSからなる群から選択される薬剤からなる群から選択される少なくとも1種の化合物をさらに含む、請求項１２又は１３記載の医薬組成物。
  15. ケネディ病、ヘリコバクターピロリ感染を伴う又は伴わない十二指腸癌、結腸直腸癌、ゾリンジャー・エリソン症候群、ヘリコバクターピロリ感染を伴う又は伴わない胃癌、病原性精神病的病態、統合失調症、不妊、新生物、炎症性宿主反応、癌、悪性転移、メラノーマ、乾癬、液性及び細胞仲介性免疫応答障害、内皮内の白血球接着及び遊走プロセス、摂食障害、睡眠-覚醒障害、エネルギー代謝の恒常性制御障害、自律神経機能障害、ホルモン平衡障害又は体液の調節障害、多発性硬化症、ギラン・バレー症候群、及び慢性炎症性脱髄性多発性神経根症からなる群から選択される疾病の治療において使用するための、請求項１〜１０のいずれか一項記載の化合物又は請求項１２〜１４のいずれか一項記載の医薬組成物。
  16. 軽度認知障害、アルツハイマー病、家族性英国型認知症、家族性デンマーク型認知症、ダウン症候群における神経変性、及びハンチントン病からなる群から選択される疾病の治療において使用するための、請求項１〜１０のいずれか一項記載の化合物又は請求項１２〜１４のいずれか一項記載の医薬組成物。
  17. 関節リウマチ、アテローム性動脈硬化、膵炎、及び再狭窄からなる群から選択される疾病の治療において使用するための、請求項１〜１０のいずれか一項記載の化合物又は請求項１２〜１４のいずれか一項記載の医薬組成物。
  18. 下記を含む、請求項１〜１０のいずれか一項記載の式(I)の化合物の製造方法：
    (a)R2が=Oを表す式(I)の化合物を、式(II)の化合物から製造し、
    Figure 2014508184
     （式中、Ra、n、及びR1は請求項１で定義されたとおりであり、Alkはエチル又はブチル基を表す）、それに続いて脱保護反応を行うこと；又は
    (b)式(I)の化合物の相互変換;及び/又は
    (c)保護されている式(I)の化合物を脱保護すること。
JP2013558454A 2011-03-16 2012-03-16 グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 Active JP6050264B2 (ja)

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US201161453333P 2011-03-16 2011-03-16
US61/453,333 2011-03-16
PCT/EP2012/054631 WO2012123563A1 (en) 2011-03-16 2012-03-16 Benz imidazole derivatives as inhibitors of glutaminyl cyclase

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JP2014508184A5 true JP2014508184A5 (ja) 2015-05-07
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DK (1) DK2686313T3 (ja)
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