JP2020517688A - NrfおよびHIF活性化剤/HDAC阻害剤ならびにそれを使用した治療法 - Google Patents
NrfおよびHIF活性化剤/HDAC阻害剤ならびにそれを使用した治療法 Download PDFInfo
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Physics & Mathematics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
Abstract
Description
本発明は、米国国立衛生研究所によって授与された契約番号R01 NS079183の下で政府の支援を受けてなされた。政府は、本発明におけるある特定の権利を有する。
本出願は、その全体が参照により本明細書に援用される2017年4月26日出願の米国仮特許出願第62/490,101号の利益を請求する。
−CO2アルキル、シクロアルキル、イミノ、アミド、トリフルオロメチル、アリール、およびヘテロアリールから独立して選択される1つ以上の基、特に、1〜5個の基で置換することができる。例示的なアリール基としては、フェニル、クロロフェニル、メチルフェニル、メトキシフェニル、トリフルオロメチルフェニル、ニトロフェニル、2,4−メトキシクロロフェニルなどが挙げられるが、これらに限定されない。
次の合成スキームは、本化合物を合成するために使用される反応を代表する。本発明の化合物を調製するための変法および代替スキームは容易に、当業者の能力の範囲内である。
合成方法および手順
手順
1H NMRスペクトルおよび13C NMRスペクトルは、内部標準としてTMSを用いて、それぞれ400MHzおよび100MHzで、Bruker分光計で記録した。多重度を示す標準的な略語を次のように使用した:s=一重線、b.s=広い一重線、d=二重線、t=三重線、q=四重線、m=多重線。HRMS実験は、LTO−FTICRまたはShimadzu IT−TOF質量分析計で実施した。TLCは、Merck250mm60F254シリカゲルプレートを使用して実施した。Analtech1000mmシリカゲルGFプレートを使用して分取TLCを実施した。カラムクロマトグラフィーは、Merckシリカゲル(40〜60メッシュ)を使用して実施した。分析用HPLCは、Ace3AQカラム(100×4.6mm)で、ダイオードアレイ検出器を備えたShimadzu10VPシリーズHPLCを用いて実施し、流量=2.0mL/分、水中10%アセトニトリル10分間から0.05%TFA含有100%アセトニトリル5分間まで(方法A)、または水中30%アセトニトリルから0.05%TFA含有100%アセトニトリル15分間まで(方法B)または水中30%アセトニトリルから0.05%TFA含有100%アセトニトリル30分間まで(方法C)で、この最後の方法ではカラムAceAQ5(250×10mm)を使用した。
ヒトHDAC1(GenBank受入番号NM_004964):C末端GSTタグ付きの全長、分子量=79.9kDa、Sf9細胞のバキュロウイルス発現系により発現。酵素は、50mMトリスHCl、pH8.0、138mM NaCl、20mMグルタチオン、および10%グリセロール中にあり、−80℃で6か月超安定である。SDS−PAGEによる純度は10%超である。比活性は、20U/μgであり、25mMトリス/Cl、pH8.0、137mM NaCl、2.7mM KCl、1mM MgCl2、0.1mg/ml BSA、100μM HDAC基質、および13.2ng/μl HDAC1、30℃で30分間のインキュベーションのアッセイ条件下で1U=1pmol/分である。
HDAC1:75nM HDAC1および50μM HDAC基質は、反応緩衝液中にあり、最後に1%DMSOとする。30℃で2時間インキュベートする。
すべてのIC50値は、GraphPad Prism第5版およびS字状用量反応式(可変性のある傾き)
Y=最小値+(最大値−最小値)/(1+10^((LogEC50−X)*HillSlope))を使用して自動的に計算し、式中、Xは濃度の対数であり、Yは応答であり、Yは最小値から始まり、S字状で最大値へと移動する。ほとんどの場合、「最小値」は0に設定され、「最大値」は「120%未満」に設定される。これは、「4パラメータ算定式」と同じである。GraphPad Prismを使用してIC50曲線も描画し、IC50値およびHillの傾きを提供する。
すべての化合物は、HDAC1およびHDAC6の両アイソフォームに対して試験されており、それらのIC50値を表1に示す。選択されたHDACisは、すべてのアイソフォームに対して特徴づけられている。
N2a細胞を100nMの種々の試験化合物でON処理し、DMSO処理細胞と比較した。RIPA緩衝液を使用して細胞を収集した。Image QuantTLを使用してWBを分析し、アセチル化チューブリンの強度とチューブリンバンドの強度との間の比率を計算した。これらの比率を、DMSOの値に対して標準化した(倍数増加)。各試料について、50μgのタンパク質を12%SDS−PAGEゲルにロードし、PVDF膜上にブロットした。アセチル化α−チューブリンおよびα−チューブリンの積分密度を、Image Jソフトウェアを使用してWB上で測定した。さらに、アセチル化α−チューブリンの積分密度とα−チューブリンの積分密度との間の比率を計算した。表1は、チューブリンのアセチル化試験の結果をまとめている。
化合物II−ING−66を、ホモシステイン酸(HCA)によって誘導される酸化ストレスのモデルにおいて検査し、本モデルでは、ニューロンを試験化合物単独でまたはHCAの存在下で処理した。MTTアッセイを使用して細胞生存度を評価したので、結果を図1にまとめている。
血液脳関門(BBB)を通過する本化合物の能力を決定するために、試験を実施した。特に、マウス1に、DMSO中の化合物II−ING−6約7.5mg/kgを静脈内注射した。マウス2では、約10mg/kgとした。血液、脳、肝臓を20分後に収集した(表4)。
II−ING−6がBBBを通過することができるという別の証拠は、SC(Frontiers in Neuroscience 2011,5(103),p.1−4)実験から得た。SCは、マウスに一連の課題を提供し、1時間の試験セッションの間に2,000を超える特長を捉える。これらの特長を、マウスの行動の研究を自動化するコンピュータアルゴリズムおよびデータマイニングアプローチで解析し、抗うつ薬、向知性薬、抗精神病薬、抗不安薬を含む一連の多様な参照化合物を使用して得た行動シグネチャのデータベースと比較する。このアッセイにおいて、C57BL/6マウスに化合物II−ING−6を50mg/kg(腹腔内)で注射した。頑強なSCシグネチャを得、この化合物が抗不安作用を有することを示した。結果を図4にまとめている。
化合物II−ING−6を遺伝毒性アッセイにおいて試験し、化合物の変異原性能を評価した。Ames試験を、TA98−S9、TA100−S9、TA1535−S9、およびTA1537−S9のようないくつかの細菌株を用いて行った。各実験において、適宜、それぞれの参照化合物をII−ING−6と同時に試験し、データをEurofin Incで決定された履歴値と比較した。本化合物を0.6〜100μMの濃度で試験した陰性試験結果は、化合物II−ING−6が変異原性ではないことを立証した。
また、化合物II−ING−6を、43のクローン化ヒトおよびげっ歯類中枢神経系受容体、チャネル、および輸送体のパネルにおいて、NIMH後援の向精神薬スクリーニングプログラム(PDSP)を使用して試験した。これらのアッセイにおいて有意な活性は認められなかった。
Nrf2標的遺伝子の発現を、II−ING−66(25mg/kg腹腔内)を投与した3か月齢の雄C57BL/6マウスにおいて評価した。RT−PCRによる分析は、腹側中脳および線条体におけるHmox−1およびNQO1の有意な増加を示した。Hmox−1発現は、肝臓においても有意に上方調節された。これらのインビボでのデータは、フェニルヒドロキサマートHDAC阻害剤によるHIF−1αおよびNrf2の活性化のインビトロでの観察を支持している(Gaisina et al,ACS Chem.Neurosci.2017)。
Claims (46)
- 構造式
互いにオルトに位置する2つのY基が、それらの結合する炭素原子と一緒になって、O、SおよびNRaから選択される1つもしくは2つのヘテロ原子を含有する5員もしくは6員の炭素環または5員もしくは6員の複素環を形成し、
mは、整数0、1、2、3、または4であり、
Zは、独立して、ハロ、−OH、−CN、−NO2、C1〜6アルキル、アリール、ヘテロアリール、−ORa、−N(Ra)2、−NHRa、−CO−N(Ra)2、−NHCO−Ra、−CO2Ra、−SRa、−OCORa、−NHSO2Ra、−SO2N(Ra)2、および−SO2Raからなる群から選択され、あるいは
互いにオルトに位置する2つのZ基が、それらの結合する炭素原子と一緒になって、O、SおよびNRaから選択される1つもしくは2つのヘテロ原子を含有する5員もしくは6員の炭素環または5員もしくは6員の複素環を形成し、
nが、整数0、1、2、3、または4であり、
R1およびR2が、独立して、水素、ハロ、またはC1〜6アルキルであり、あるいはR1が5員または6員の含窒素環であり、R2が水素、ハロ、またはC1〜6アルキルであり、あるいはR1およびR2が、それらの結合する炭素原子と一緒になって、3員〜6員の炭素環または複素環を形成し、
Raが、水素、C1〜6アルキル、アリール、またはヘテロアリールであり、
R3が、水素、C1〜6アルキル、−CH2アリール、アリール、またはヘテロアリールであり、
R4が、水素またはハロであり、
R5が、C1〜3アルキルまたはアリールである、
化合物、あるいはその薬学的に許容される塩。 - Yがなし、Cl、F、−OCH3、−OBn、−NO2、−N(CH3)2、−NHSO2CH3、−SCH3、−C6H5、
- 互いにオルトである2つのY基が一緒になって
- mが2であり、各Yがハロである、請求項1に記載の化合物。
- 第1のYがFであり、第2のYがClである、請求項4に記載の化合物。
- mが0、1、または2である、請求項1〜5のいずれか1項に記載の化合物。
- R1およびR2がそれぞれ水素であり、それぞれメチルであり、それぞれフルオロであるか、またはそれらの結合する炭素と一緒になってシクロプロピル基を形成する、請求項1〜6のいずれか1項に記載の化合物。
- R3がH、−CH3、または−CH2C6H5である、請求項1〜7のいずれか1項に記載の化合物。
- R4がHまたはFである、請求項1〜8のいずれか1項に記載の化合物。
- R5が−CH3または−C6H5である、請求項1〜9のいずれか1項に記載の化合物。
- Zが、なし、Cl、または−OCH3である、請求項1〜10のいずれか1項に記載の化合物。
-
- (a)請求項1に記載の化合物と、(b)HDACの阻害ならびに/またはNrf2およびHIFの活性化が利益を提供する疾患または容態の処置において有用な第2の治療薬と、(c)場合により賦形剤および/または薬学的に許容される担体と、を含む、組成物。
- 前記第2の治療薬が、癌の処置において有用な化学療法薬を含む、請求項13に記載の組成物。
- 請求項1に記載の化合物と、薬学的に許容される担体またはビヒクルと、を含む医薬組成物。
- HDACの阻害ならびに/またはNrf2およびHIFの活性化が利益を提供する疾患または容態を治療する方法であって、それを必要とする個体へ、治療有効量の請求項1に記載の化合物を投与することを含む、方法。
- 前記疾患または容態が、HDACの阻害ならびにNrf2およびHIFの活性化により利益を得る、請求項16に記載の方法。
- 前記HDACがHDAC6である、請求項16に記載の方法。
- 前記疾患または容態の処置において有用な治療有効量の第2の治療薬を投与することをさらに含む、請求項16に記載の方法。
- 請求項1に記載の化合物および前記第2の治療薬が同時に投与される、請求項19に記載の方法。
- 請求項1に記載の化合物および前記第2の治療薬が別々に投与される、請求項19に記載の方法。
- 前記疾患または容態が癌である、請求項16に記載の方法。
- 前記疾患が癌であり、前記第2の治療薬が化学療法薬、放射線、および免疫療法のうちの1つ以上である、請求項19に記載の方法。
- 前記第2の治療薬が放射線を含み、前記放射線が場合により、本明細書の段落[0206]〜段落[0210]に開示されている放射線増感剤および/または治療薬と併用して投与される、請求項23に記載の方法。
- 前記癌が、本明細書の段落[0192]および段落[0194]〜段落[0201]に開示されている癌から選択される、請求項22に記載の方法。
- 記化学療法薬が、段落[0223]〜段落[0227]および段落[0231]〜段落[0234]に開示されている抗癌薬から選択される、請求項23に記載の方法。
- 前記疾患または容態が、神経疾患、神経変性障害、末梢神経障害、または外傷性脳損傷である、請求項16に記載の方法。
- 前記疾患または容態が、本明細書の段落[0241]〜[0246]に開示されている疾患または容態から選択される、請求項27に記載の方法。
- 前記疾患または容態が、卒中である、請求項16に記載の方法。
- 前記疾患または容態が、炎症または自己免疫疾患である、請求項16に記載の方法。
- 前記自己免疫疾患または炎症が、段落[0256]および段落[0257]に開示されている容態から選択される、請求項30に記載の方法。
- 前記自己免疫疾患または前記炎症の処置において有用な治療有効量の第2の治療薬を投与することをさらに含む、請求項31に記載の方法。
- 前記第2の治療薬が、段落[0262]に開示されている薬剤から選択される、請求項32に記載の方法。
- 前記疾患または容態が、段落[0067]および[0185]に開示されている、請求項16に記載の方法。
- 前記疾患または容態が、寄生虫感染症である、請求項16に記載の方法。
- 前記寄生虫感染症が、マラリア、トキソプラズマ症、トリパノソーマ症、蠕虫病、または原虫感染症である、請求項35に記載の方法。
- 前記個体へ、アリールアミノアルコール、シンコナアルカロイド、4−アミノキノリン、1型または2型葉酸合成阻害薬、8−アミノキノリン、抗菌薬、過酸化物、ナフトキノン、および鉄キレート剤からなる群から選択される抗マラリア化合物を併用投与することをさらに含む、請求項36に記載の方法。
- 前記個体へ、キニーネ、キニジン、メフロキン、ハロファントリン、クロロキン、アモジアキン、プログアニル、クロロプログアニル、ピリメタミン、プリマキン、8−[(4−アミノ−1−メチルブチル)アミンブ(aminb)]−2,6−ジメトキシ−4−メチル−5−[(3−トリフルオロメチル)フェノキシ]キノリンスクシナート(WR238,605)、テトラサイクリン、ドキシサイクリン、クリンダマイシン、アジスロマイシン、フルオロキノロン、アルテメテル、アルテエテル、アルテスナート、アルテリン酸、アトバコン、およびデスフェリオキサミンからなる群から選択される抗マラリア化合物を併用投与することをさらに含む、請求項36に記載の方法。
- クロロキンを前記個体へ併用投与することをさらに含む、請求項36に記載の方法。
- 前記疾患または容態が、自閉症または自閉症スペクトラム障害である、請求項16に記載の方法。
- 放射線療法および/または化学療法の細胞毒性効果に対する癌細胞の感受性を上昇させる方法であって、前記癌細胞を、前記放射線療法および/または前記化学療法に対する前記癌細胞の前記感受性を上昇させるのに十分な量の請求項1に記載の化合物と接触させることを含む、方法。
- 前記細胞が、インビボ細胞である、請求項41に記載の方法。
- 免疫抑制を発生させる方法であって、有効量の請求項1に記載の化合物を、それを必要とする個体へ投与することを含む、方法。
- 前記化合物が、蛍光色素、3H、11C、18F、123I、125I、および131Iから選択される放射性同位体、分子タグ、またはこれらの混合物で標識されている、請求項1に記載の化合物。
- 前記標識が11C−メチル基を含む、請求項44に記載の化合物。
- (a)請求項1に記載の放射性標識化合物を提供することと、
(b)細胞または組織を前記放射性標識化合物と接触させることと、
(c)前記接触させた細胞または組織の放射線画像を作成することと、を含む、撮像方法。
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