JP6532860B2 - 癌、神経障害及び線維性障害の治療のための、脂質フラン、ピロール及びチオフェン化合物 - Google Patents
癌、神経障害及び線維性障害の治療のための、脂質フラン、ピロール及びチオフェン化合物 Download PDFInfo
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Description
本出願は、2013年3月29日に出願された米国仮特許出願第61/853,163号に関連し、利益を主張する。本仮出願の全体は、参照として本明細書に組み込まれる。
本発明は、癌、神経障害、及び線維性障害の治療のための化合物、方法、及び組成物に関する。
式中、
各Zは独立して、O、S、またはNR5であり、
R1、R2、R3、及びR4は、同じものか、または異なるものであり、別々に水素原子、C1−C35アルキル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17、C1−C35アルケニル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17、または、C1−C35アルキニル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17を表し、アルキル、アルケニル、またはアルキニル部分は、1つ以上のハロゲン(F、Cl、Br、またはI、より典型的にはF)で、及び/またはエポキシド(例えば、炭素鎖に2価の結合をした酸素)、ヒドロキシル、もしくは保護されたヒドロキシル(OR5)、チオール、もしくは保護されたチオール(SR5)、アミン(NR5R6)、アルデヒド(−CHO)、ケトン(−COR5)、アセチル(−O−CO−R5)、またはエステル(−C(O)OR5)官能基からなる群から選択される1つ以上の部分により任意に置換され、式中、R5及びR6は別々に、水素原子、C1−C35、より典型的にはC1−C20アルキル基、有利にはC10−C22、より有利にはC12−C20、さらに有利にはC13−C17、またはC1−C35アルケニル基、有利にはC10−C22、より有利にはC12−C20、さらに有利にはC13−C17を表す。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されたように任意に置換される、2つ以上の二重結合を含むC9−C20アルキル鎖である。
R1は、上で定義されたように任意に置換される、2つ以上の二重結合を含むC9−C20アルキル鎖である。
R1は、上で定義されたように任意に置換される、2つ以上の二重結合を含むC9−C20アルキル鎖である。
A)対象における癌細胞の増殖の阻害に使用するための、本明細書に記載されるような、式I、II、またはIIIの化合物、及び薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
B)対象における癌細胞の遊走の阻害に使用するための、本明細書に記載されるような、式I、II、またはIIIの化合物、及び薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
C)癌の治療における化学療法剤として使用するための、本明細書に記載されるような化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
D)癌を治療するための治療管理体制を受けている対象において、もう1つの化学療法剤を組み合わせるのに使用するための、本明細書に記載されるような化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
E)癌を有する対象を治療するための化学療法剤として使用する薬剤の製造における、本明細書に記載される化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグの使用。
F)癌を有する対象の治療に使用するための、本明細書に記載される有効量の化合物を含有する治療用製品の調製のためのプロセス。
G)癌の治療用化学療法剤としての治療的使用を目的とする、本明細書に記載される化合物から選択される薬剤の製造方法。
H)神経障害を患う対象の治療に使用するための、本明細書に記載されるような、式I、II、またはIIIの化合物、及び薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
I)神経障害を有する対象の治療薬として使用されるための薬剤の製造における、本明細書に記載される化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、もしくはプロドラッグの使用。
J)神経障害を有する対象の治療に使用するための、本明細書に記載される化合物を有効量含有する治療用製品の調製プロセス。
K)神経障害の治療における治療的使用を目的とする、本明細書に記載される化合物から選択される薬剤の製造方法。
L)線維性障害を患う対象の治療に使用するための、本明細書に記載されるような、式I、II、またはIIIの化合物、及び薬学的に許容される、それらの組成物、塩、同位体類似体、またはプロドラッグ。一実施形態では、化合物は式I(n)である。
M)線維性障害を有する対象における治療薬として使用されるための薬剤の製造における、本明細書に記載される化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、もしくはプロドラッグの使用。
N)線維性障害を有する対象の治療に使用するための、本明細書に記載される化合物を有効量含有する治療用製品の調製プロセス。
O)線維性障害の治療における治療的使用を目的とする、本明細書に記載される化合物から選択される薬剤の製造方法。
P)活性成分が植物抽出物の混合物または組み合わせとして提供されず、その代わりに活性成分は高度な純粋形態で送達される、固形腫瘍、神経障害、または線維性障害を治療するのに使用するための、本明細書に記載されるような化合物。一実施形態では、本発明は、固形腫瘍、神経障害、または線維性障害の治療のための剤形であり、活性化合物が、充填剤、安定剤、または他の非活性または不活性成分を考慮せずに、少なくとも96%、97%、98%、または99%の純度を有する。代替的実施形態では、剤形は、2つ以上の活性成分を有し、前記活性成分の1つのみが、本明細書に記載されるような式I、II、またはIIIの化合物から選択される。
特に指示しない限り、明細書及び特許請求の範囲を含む本出願で使用される次の用語は、以下に与えられる定義を有する。本明細書中及び本添付の特許請求の範囲で使用される場合、単数形「a」、「an」、及び「the」は、文脈が明らかに別途指示しない限り、複数の指示対象を含む。標準的な化学用語の定義は、Carey and Sundberg(2007)Advanced Organic Chemistry 5th Ed.Vols.A and B,Springer Science+Business Media LLC,New Yorkを含む参照著作物に見出すことができる。本発明の実施は、特に指示がない限り、合成有機化学、質量分析、クロマトグラフィーの分離及び分析方法、タンパク質化学、生化学、組換えDNA技術、ならびに薬理学の通常の方法を用いるであろう。有機化学の通常の方法は、March’s Advanced Organic Chemistry:Reactions,Mechanisms,and Structure,6th Edition,M.B.Smith and J.March,John Wiley&Sons,Inc.,Hoboken,NJ,2007に含まれるものを含む。
一実施形態では、本発明は、化合物、または、かかる式I、II、またはIIIの化合物の、本明細書に記載されるような使用に関し、
各Zは独立して、O、S、またはNR5であり、
R1、R2、R3、及びR4は、同じものか、または異なるものであり、別々に水素原子、C1−C35アルキル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17、C1−C35アルケニル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17、または、C1−C35アルキニル基、有利には、C10−C22、より有利には、C12−C20、さらに有利には、C13−C17を表し、アルキル、アルケニル、またはアルキニル部分は、1つ以上のハロゲン(F、Cl、Br、またはI、より典型的にはF)で、及び/またはエポキシド(例えば、炭素鎖に二重結合した酸素)、ヒドロキシル、もしくは保護されたヒドロキシル(OR5)、チオール、もしくは保護されたチオール(SR5)、アミン(NR5R6)、アルデヒド(−CHO)、ケトン(−COR5)、アセチル(−O−CO−R5)、またはエステル(−C(O)OR5)官能基からなる群から選択される1つ以上の部分により任意に置換され、式中、R5及びR6は別々に、水素原子、C1−C35、より典型的にはC1−C20アルキル基、有利にはC10−C22、より有利にはC12−C20、さらに有利にはC13−C17、またはC1−C35アルケニル基、有利にはC10−C22、より有利にはC12−C20、さらに有利にはC13−C17を表す。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4=上で定義されるように任意に置換されるC13−C19アルキルである。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C9−C20不飽和アルキル鎖であり、
−CH=CH(CH2)mCH3、
上で定義されるように任意に置換され、
式中、
m=6〜17である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C13−C19不飽和アルキル鎖であり、
−CH=CH(CH2)mCH3、
上で定義されるように任意に置換され、
式中、
m=10〜16である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C9−C20不飽和アルキル鎖であり、
−(CH2)n−CH=CH(CH2)mCH3、
上で定義されるように任意に置換され、
式中、
n=1〜17であり、
m=1〜17である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C13−C19不飽和アルキル鎖であり、
−(CH2)n−CH=CH(CH2)mCH3、
上で定義されるように任意に置換され、
式中、
n=1〜15であり、
m=1〜15である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C9−C20不飽和アルキル鎖であり、
−(CH2)mCH=CH2、
上で定義されるように任意に置換され、
式中、
m=7〜18である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、以下の式の単一の二重結合を有する直鎖C13−C19不飽和アルキル鎖であり、
−(CH2)mCH=CH2、
上で定義されるように任意に置換され、
式中、
m=11〜17である。
一部の実施形態では、化合物は、以下の式I(h)を有し、
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換された、2つ以上の二重結合を含むC9−C20アルキル鎖である。
一部の実施形態では、化合物は、以下の式I(i)を有し、
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換された、2つ以上の二重結合を含むC13−C19アルキル鎖である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換される、1つ以上の三重結合を含むC9−C20アルキル鎖である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換される、1つ以上の三重結合を含むC13−C19アルキル鎖である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換される、1つ以上の二重結合及び1つ以上の三重結合を含むC9−C20アルキル鎖である。
Zは独立して、O、S、NR5であり、
R1=R2=R3=Hであり、
R4は、上で定義されるように任意に置換される、1つ以上の二重結合及び1つ以上の三重結合を含むC13−C19アルキル鎖である。
本発明は、同位体が自然の存在割合を超える、すなわち豊富な量で、原子が所望の同位体置換された、化合物及び化合物の使用を含む。同位体は、質量数が異なる以外同じ原子番号、すなわち中性子数が異なる以外同じ陽子数を有する原子である。一般的例により、かつ限定なしに、水素の同位体、例えば、重水素(2H)及び三重水素(3H)は、記載された構造のどこにでも使用してよい。代わりにまたは加えて、炭素の同位体、例えば、13C及び14Cを使用してもよい。好ましい同位体置換は、薬物の性能を向上させるために、分子上の1つ以上の位置にある水素に対する重水素である。重水素は、代謝の際の結合の切断位置に(α−重水素速度論的同位体効果)、または結合の切断部位に隣接して、もしくは近くに(β−重水素速度論的同位体効果)結合される場合がある。
癌を治療するための化合物、方法、及び組成物を提供する。癌細胞の細胞遊走を阻害するための、改良された化合物、方法、及び組成物を提供する。浸潤癌を阻害する、改良された化合物、方法、及び組成物を提供する。異常な細胞増殖を阻害するための、改良された化合物、方法、及び組成物を提供する。一実施形態では、癌は固形腫瘍である。一実施形態では、固形腫瘍は非皮膚腫瘍である。
日光角化症(AKs)は、主として過度の紫外線(UV)暴露により生じる、扁平上皮癌(SCC)、及び他の皮膚の悪性腫瘍を発症するリスクの増加を予告する一般的な皮膚病変である。それらは、主に色白の個体に見られ、増加する免疫抑制の問題である。日光角化症(AKs)は、自然に消失するか、安定を保つか、または浸潤性SCCへと変化する場合がある。
本発明の一態様では、本明細書に開示される化合物は有益に、有益な、付加的、または相乗効果を求めて、別の治療レジメンと組み合わせて投与することができる。
本明細書に開示される化合物のさらなる治療的使用としては、神経障害の治療及び/または予防における使用が挙げられる。これらは、細胞組織の変形が共通項である、アルツハイマー病及びパーキンソン病などの認知障害から、剥脱性緑内障などの目の疾患にまで及ぶ。一実施形態では、有効量の本明細書に記載される化合物を投与することを含む、神経障害を治療する方法が、本明細書で提供される。一実施形態では、神経障害は、アルツハイマー病である。一実施形態では、神経障害は、パーキンソン病である。一実施形態では、神経障害は、筋萎縮性側索硬化症である。一実施形態では、神経障害は、浮腫、障害、または外傷から生じる、中枢または末梢神経系の損傷、機能不全、または合併症である。一実施形態では、神経障害は、多発性硬化症、アルツハイマー病、筋萎縮性側索硬化症、パーキンソン病、ハンチントン舞踏病、神経障害性疼痛、または脊髄損傷である。本発明の一実施形態では、神経障害の治療のための化合物は、本明細書に記載されるような式I、II、もしくはIIIの化合物、または薬学的に許容される、それらの組成物、塩、同位体類似体、もしくはプロドラッグから選択される。一非限定的実施例では、神経障害は、本明細書に記載されるような式I(a)、式I(b)、式I(c)、式I(d)、式I(e)、式I(f)、式I(g)、式I(h)、式I(i)、式I(j)、式I(k)、式I(l)、式I(m)、式I(n)、式I(o)、式I(p)、式I(q)、式I(r)、式I(s)、式I(t)、式I(u)、式I(v)、式I(w)、式I(x)、式I(y)、式I(z)、式I(aa)、式I(ab)、式I(ac)、式I(ad)、式I(ae)、式I(af)、式I(ag)、式I(ah)、式I(ai)、式I(aj)、式I(ak)、式I(al)、式I(am)、式I(an)、もしくは式I(ao)、または薬学的に許容される、それらの組成物、塩、同位体類似体、もしくはプロドラッグで治療される。
本発明の一態様では、本明細書に開示される化合物は有益に、神経障害を治療するための、有益な、付加的、または相乗効果を求めて、1つ以上の追加の治療法と組み合わせて投与することができる。治療法の組み合わせは、本明細書に記載されるような化合物を、神経障害を治療するために使用される治療薬で使用することを含む場合がある。神経障害の治療に使用される治療法としては、Abstral、Aggrenox、Aggrenox、Ampyra、Amrix、Anexsia、Apokyn、Aptiom、ARICEPT、Avinza、Avonex、Axert、Axona、Banzel、Botox、Bromfenac、Butrans、Cambia、Carbaglu、Carbatrol、Cenestin、Cialis、Clonazepam、Comtan、Copaxone、Cuvposa、Cylert、Depakote、Durezol、Edluar、Eliquis、Embeda、Exalgo、Exelon、Exparel、Extavia、Fetzima、Focalin、Frova、Fycompa、Galzin、Gralise、Hetlioz、Horizant、Imitrex、Intermezzo、Intuniv、Invega、Iontocaine、Kadian、Kapvay、Levetiracetam、Lamictal、Lazanda、Levitra、Lidoderm Patch、Lunesta、Lupron Depot、Lusedra、Lyrica、Maxalt、Metadate CD、Migranal、Mirapex、Myobloc、Naltrexone HCl、Namenda、Neupro、Neurontin、NORCO tablets、Northera、Novantrone、Nucynta、Nuedexta、Nuvigil、Nymalize、Onfi、Onsolis、Oxecta、Oxtellar XR、Oxycodone及びAspirin、Poicor、Potiga、Pramipexole、Quadramet、Quillivant XR、Qutenza、Rebif、Redux、Relpax、Reminyl、Requip、Rilutek、Rozerem、Sabril、Selegiline、Silenor、Sonata、Sprix、Stavzor、Strattera、Subsys、Tasmar、Tegretol、Tivorbex、Topamax、Trileptal、Trokendi XR、Tysabri、Ultracet、UltraJect、VERSED、Viibryd、Vimpat、Vivitrol、Vpriv、Vyvanse、Xenazine、Xifaxan、Xyrem、Zanaflex、Zipsor、Zohydro ER、Zomig、Zonegran、ならびにZubsolvが挙げられるが、これらに限定されない。
一実施形態では、有効量の本明細書に記載される化合物を投与することを含む、線維性障害を治療及び/または予防する方法が、本明細書で提供される。
本発明の一態様では、本明細書に開示される化合物は有益に、有益な、付加的、または相乗効果を提供するために、線維性障害を治療するために使用される1つ以上の治療法と組み合わせて投与することができる。線維性障害の治療に使用される治療法としては、プレドニゾン、シクロフォスアミド(Cytoxan(商標))、アザチオプリン(Imuran(商標))、N−アセチルシステイン(NAC)及びピルフェニドン(Esbriet(商標)、Pirfenex(商標)、Pirespa(商標))などのコルチコステロイドが挙げられるが、これらに限定されない。
一態様では、本発明は、薬学的有効量の本発明の化合物及び薬学的に許容される担体を含む薬学的組成物を提供する。
活性化合物の調製
開示された化合物は、以下の一般式により作製することができる。
2−(8Z,11Z−ヘプタデカジエニル)フランの合成(スキーム1)
ステップ1.高純度リノール酸の調製
A1)天然のブドウ種子(60%非共役−10%共役)またはベニバナ(60%非共役−10%共役)から供給される共役(「c」)及び優先的に非共役(「nc」)リノール酸(C18)を得る。
B)植物油を、0.5%重量/重量のカンジダ・ルゴサ酵素(Amano12K)を加えている精製水と2:1で混合するか、または固定された酵素層を使用して、水及び油混合物を再循環させる。両実施例において、窒素雰囲気で40℃以下及び35℃以上の温度を維持した。酵素を自由に混合し、次にミキシングに保持した場合、それが60秒ごとの容器内容物の完全な再循環を可能にし、24時間継続する。反応を中断し、ヘプタンまたは他の非極性溶媒を溶液に加え(約0.5:1の比率)、窒素及び微光下で撹拌し、デカントする。3回繰り返して、脂肪酸を得る。窒素下で、溶媒を蒸発させる。
A2)交互に及び優先的に、90%の非共役及び10%の共役として分布する、主にリノール酸(75%)であるトール油脂肪酸を得る。
C)BでまたはA2で得られた脂肪酸を混合し、1部の脂肪酸対3部のアセトン(重量:重量)の比率のアセトンと混合し、1〜6時間で−40℃に至らせ、−40℃で48時間保持する。
D)−35℃未満に冷却しながら、公称5〜15マイクロメートルフィルターを使用して真空濾過する。溶媒を蒸発させて、非常に高純度なリノール酸(>95℃)を回収する。
E)標準的な分離手順を用いて、フラッシュクロマトグラフィーまたは臨界流体クロマトグラフィーで、99%の純粋リノール酸(非共役)を回収する。
A)5部のDMF(ジメチルホルムアミド)を、12,000部の冷却した(5℃)シクロヘキサン及び3000部の冷却した(5℃)リノール酸に加え、氷浴中において、0.2〜0.4L/分の窒素気流下で撹拌する。
B)冷却した(5℃)塩化チオニル、SOCl2を3〜4mL/分で滴加する。
C)全ての塩化チオニルを加えた後、氷浴を室温になるに任せ、24時間または全てのガスの放出が停止するまで、窒素気流下で撹拌し続ける。
D)タール層からシクロヘキサンをデカントし、窒素下で蒸発させて、透明琥珀色の液体を回収した。ガラス容器によく密閉して保存する。生成物を90%の収率で得る。
A)C5H5NOS(オマジンナトリウム)及びBrCCl3(ブロモトリクロルメタン)を、ガラス容器中で共に混合し、5℃で24時間定置して、結晶形成を促す。
B)ステップAの混合物を、氷浴で冷却した5℃のシクロヘキサンに加え、0.1〜0.3L/分の窒素流を開始する。
C)冷却した5℃のステップ2の)リノール酸クロリドを、3〜4ml/分以下で、ステップBの反応混合物に滴加する。
D)ステップ2のリノール酸クロリドを加えた後、窒素流下で撹拌し続ける。氷浴を溶けるに任せる。
E)ブロモジエンの形成を示す黄色/赤色への色の変化を注意深く観察する。
F)デカントすることをさらに加え、フラッシュクロマトグラフィーを使用して、ブロモジエンを回収する。生成物を50%の収率で単離した。
1)1Mのブチルリチウムのヘキサン溶液を調製する。注意:凝固するのを防ぐために、10℃未満に冷却してはならない。
2)冷却した5℃のフランを、冷却した5℃のTHFに加える。
3)氷浴を維持する。
4)ヘキサン中のブチルリチウムを、約3〜4ml/分で、冷却したフラン/THF溶液に滴加する。
5)氷浴を維持し、全てのブチルリチウムを加えた後、2時間以下撹拌する。リチウム化したフランを90%の収率で得る。
1.約1部のシクロヘキサン及び1部のステップ3のブロモジエンを共に加え、5℃まで冷却し、毎分約0.1〜0.4Lの窒素流を開始する。温度を維持して、撹拌する。
2.冷却した5℃のステップ4のリチウム化したフランを、約3〜4ml/分で滴加する。温度及び撹拌を維持する。
3.暗赤褐色への色の変化を注意深く観察する。全てのリチウム化したフランを加えた後、反応物の冷却、窒素流、及び撹拌を1時間維持する。
4.1時間後、温度を周囲温度まで上がるに任せ、次に撹拌及び窒素を12時間維持する。
5.生成物をイソプロパノールまたはエタノールと混合した3%の食塩水(1:1)で3回洗浄し、デカントし、溶媒を蒸発させる。
6.クロマトグラフィーで精製する。
2−(8Z,11Z−ヘプタデカジエニル)チオフェンの合成(スキーム2)
ステップ1〜3は、実施例1に記載されているように実施する。
1)1Mのブチルリチウムのヘキサン溶液を調製する。注意:凝固するのを防ぐために、10℃未満に冷却してはならない。
2)冷却した5℃のチオペンを、冷却した5℃のシクロヘキサンに加える。
3)氷浴を維持する。
4)ヘキサン中のブチルリチウムを、約3〜4ml/分で冷却したチオペン/シクロヘキサン溶液に滴加する。
5)氷浴を維持し、全てのブチルリチウムを加えた後、2時間以下撹拌する。
6)標準的な方法で処理し、生成物を得る。
1.約1部のシクロヘキサン及び1部のステップ3のブロモジエンを共に加え、5℃まで冷却し、毎分約0.1〜0.4Lの窒素流を開始する。温度を維持して、撹拌する。
2.冷却した5℃のステップ4のリチウム化したチオフェンを、約3〜4ml/分で滴加する。温度及び撹拌を維持する。
3.全てのリチウム化したチオペンを加えた後、反応物の冷却、窒素流、及び撹拌を1時間維持する。
4.1時間後、温度を周囲温度まで上がるに任せ、次に撹拌及び窒素を12時間維持する。
5.生成物をイソプロパノールまたはエタノールと混合した3%の食塩水(1:1)で3回洗浄し、デカントし、溶媒を蒸発させる。
6.クロマトグラフィーで精製する。生成物を85%の収率で得た。
2−(8Z,11Z−ヘプタデカジエニル)ピロールの合成(スキーム3)
ステップ1:トルエン(75ml)中のピロール(2.0g、29.8mmol)8Z,11Z−ヘキサデアジエノイック酸(17.83g、44.7mmol)及び亜鉛粉末(3.88g、59.7mmol)の混合物は、ピロールが薄層クロマトグラフィーまたはHPLCで検出できなくなるまで、室温で撹拌する。反応物は、飽和重炭酸ナトリウム溶液(50ml)で急冷し、酢酸エチル(3×30ml)で抽出する。合一させた有機層は、水で洗浄し、無水Na2SO4で乾燥し、濾過し、減圧下で濃縮する。生成物は、ジクロロメタン−メタノール勾配で溶出されるシリカゲルカラムクロマトグラフィーを使用することにより精製する。
周囲温度で撹拌されるステップ1のケトン(1.63g、5.18mmol)の150mlの2−プロパノール溶液に、水素化ホウ素ナトリウム(1.34g、36.26mmol)を徐々に加える。反応物は、還流状態で加熱し、薄層クロマトグラフィーまたはHPLCにより観察する。出発物質が検出されなくなると、反応物を150mlの氷−水中に注ぎ、溶液を10%塩酸水溶液で酸性化する。反応物は、ジクロロメタン(3×50ml)で抽出する。合一させた有機抽出物は、水、食塩水で洗浄し、無水Na2SO4で乾燥し、濾過し、減圧下で濃縮する。生成物は、ジクロロメタン−メタノール勾配で溶出されるシリカゲルカラムクロマトグラフィーを使用することにより精製する。
2−(8Z,11Z−ヘプタデカジエニル)フラン製剤
本発明の一実施形態によれば、
脂質フラン製剤
本発明の別の実施形態によれば、
式I(n)は、浸潤性腫瘍の細胞遊走を阻害する
MDA−MB231及びHs578T浸潤性乳房腫瘍細胞の遊走における、式I(n)の効果は、膜浸潤培養システム(MICS)チャンバを使用して試験した。MDA−MB231細胞は、乳房腺癌細胞であり、ATCC(Cailleau R,et al.Long−term human breast carcinoma cell lines of metastatic origin:preliminary characterization.In Vitro14:911−915,1978)から入手可能である。Hs578T細胞は、乳癌細胞であり、ATCC(Hackett AJ,et al.Two syngeneic cell lines from human breast tissue:the aneuploid mammary epithelial(Hs578T)and the diploid myoepithelial(Hs578Bst)cell lines.J.Natl.Cancer Inst.58:1795−1806,1977)から入手可能である。
式I(n)は、安定な間葉系細胞表現型を活性化する
腫瘍細胞の挙動は、周囲の間質細胞の表現型ならびに上皮及び間葉系細胞型の間の相互作用により、大いに影響を受ける。式I(n)がさらに間葉系細胞に影響を及ぼすかどうかを判定するために、式I(n)の存在下での線維芽細胞の遊走能を試験した。
式I(n)は、細胞骨格の再構成を促し、腫瘍細胞増殖を阻害する
次に、式I(n)は、その細胞骨格の再構成を促す能力に関して分析する。線維芽細胞は、プレコンフルエントステージにおいて、0(図4A)、5μl(図4B)、または10μl(図4C)の式I(n)で24時間処理し、ファロイジン(アクチン−緑)、及びヨウ化プロピジウム(細胞核−赤)で染色した。式I(n)処理細胞は、対照と比較して、アクチン細胞骨格の染色強度が濃度に依存して増加すること、多数の糸状仮足、及び接着部分の染色が低下することが、細胞遊走の低下と合致することを明らかにした(http://www.cellmigration.org/science/#overview for further discussion of cell migrationを参照のこと)。
式I(n)処理細胞における、低下する局所接着キナーゼ(FAK)[Tyr576]リン酸化
MDA−MB231、Hs578T(Payne SL,Fogelgren B,Hess AR,Seftor EA,Fong SFT,Csiszar K、Hendrix MJC,and Kirschmann DA.Lysyl oxidase regulates breast cancer cell migration and adhesion through a hydrogen peroxide−mediated mechanism.Cancer Res.65:11429−36,2005)、ならびに星細胞腫細胞(Laczko R,Szauter KM,Jansen MK,Hollosi P,Muranyi M,Molnar J,Fong KSK,Hinek A,Csiszar K.Active lysyl oxidase(LOX)correlates with FAK/paxillin activation and migration in invasive astrocytes.Neuropathol Appl Neurobiol.33:631−43,2007)を含む、種々の浸潤性乳房腫瘍細胞の遊走能の低下が、局所接着キナーゼ(FAK)の活性の低下ならびにSRC及び/またはパキシリンシグナル伝達の低減のためであったことは、以前に示している。式I(n)処理細胞におけるFAK活性の状態を判定するために、5及び10μlの式I(n)で処理されたHs578T細胞におけるFAK[Tyr576]のリン酸化状態を分析した。
インビボの乳房腫瘍における化合物の有効性
乳癌のHER2駆動モデル(Muller WJ, Sinn E,Pattengale PK,Wallace R,Leder P.Single−step induction of mammary adenocarcinoma in transgenic mice bearing the activated c−neu oncogene.Cell 1988;54:105−15)は、MMTV促進剤により駆動されるc−neu(ヒトHER2のマウスオルソログ)を表現するものであるが、次の実施例で使用される。
Claims (14)
- 対象における皮膚癌、皮膚の前癌性病変または固形腫瘍を治療するための医薬組成物であって、式IIIの化合物を含んでなり、
R1は、C13−C17を含む炭素鎖を有するアルキル基またはアルケニル基を表し、かつ、
前記式IIIの化合物は、98%を超える純度を有し、
皮膚癌、皮膚の前癌性病変、または固形腫瘍が局所接着キナーゼ(FAK)を過剰発現している、医薬組成物。 - 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 前記化合物が、
- 対象における皮膚癌、皮膚の前癌性病変または固形腫瘍を治療するための医薬組成物であって、下記式の化合物:
皮膚癌、皮膚の前癌性病変、または固形腫瘍が局所接着キナーゼ(FAK)を過剰発現している、医薬組成物。 - 前記対象がヒトである、請求項1〜11のいずれか一項に記載の医薬組成物。
- 前記皮膚癌または皮膚の前癌性病変が、日光角化症、白斑症、扁平上皮細胞癌、及び基底細胞癌から選択される、請求項1〜12のいずれか一項に記載の医薬組成物。
- 前記固形腫瘍が、乳癌、肺癌および結腸癌から選択される、請求項1〜13のいずれか一項に記載の医薬組成物。
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PCT/US2014/032177 WO2014160940A2 (en) | 2013-03-29 | 2014-03-28 | Lipidic furan, pyrrole, and thiophene compounds for treatment of cancer, neurological disorders, and fibrotic disorders |
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JP (1) | JP6532860B2 (ja) |
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CN111285841A (zh) | 2013-03-29 | 2020-06-16 | 雅沃科学有限责任公司 | 用于治疗癌症、神经障碍和纤维化病症的脂类呋喃、吡咯和噻吩化合物 |
WO2017189865A1 (en) * | 2016-04-27 | 2017-11-02 | Avoscience, Llc | Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis |
KR102221789B1 (ko) * | 2019-06-27 | 2021-03-02 | 재단법인대구경북과학기술원 | 2-펜틸퓨란을 유효성분으로 함유하는 퇴행성 뇌질환 치료용 조성물 |
CN110859836B (zh) * | 2019-11-29 | 2022-04-15 | 南京林业大学 | 灵菌红素在制备淋巴管肌瘤病细胞增殖抑制剂中的应用 |
EP4274546A1 (en) * | 2021-01-06 | 2023-11-15 | The Penn State Research Foundation | Methods and materials for treating hair loss |
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CN111285841A (zh) | 2020-06-16 |
EP2978422A2 (en) | 2016-02-03 |
US10085962B2 (en) | 2018-10-02 |
WO2014160940A2 (en) | 2014-10-02 |
CN105209037A (zh) | 2015-12-30 |
CA2908505A1 (en) | 2014-10-02 |
AU2014240950A1 (en) | 2015-10-22 |
AU2014240950B2 (en) | 2018-11-01 |
US10525031B2 (en) | 2020-01-07 |
EP2978422A4 (en) | 2017-04-05 |
US20180050013A1 (en) | 2018-02-22 |
US20200237709A1 (en) | 2020-07-30 |
US20210137876A1 (en) | 2021-05-13 |
US9371302B2 (en) | 2016-06-21 |
US20160263080A1 (en) | 2016-09-15 |
US20180360798A1 (en) | 2018-12-20 |
US11058663B2 (en) | 2021-07-13 |
US9814694B2 (en) | 2017-11-14 |
JP2016515585A (ja) | 2016-05-30 |
US11833129B2 (en) | 2023-12-05 |
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