JP2022084953A - 表皮水疱症及び関連する結合組織疾患の治療におけるカンナビノイドの局所製剤の使用 - Google Patents
表皮水疱症及び関連する結合組織疾患の治療におけるカンナビノイドの局所製剤の使用 Download PDFInfo
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Abstract
Description
本出願は、その内容があらゆる目的で全体として参照によって本明細書に組み入れられる2016年5月4日に出願された米国仮特許出願番号62/331、633の利益を主張する。
疾病または状態(たとえば、単純型表皮水疱症(EBS))を治療するために
(1)治療上有効な量のカンナビノイドと、
(2)局所投与用の少なくとも1つの薬学上許容できるキャリアと、を含む、
中間径フィラメントの機能障害に関連する疾病または状態(たとえば、EBS)を治療するための局所医薬組成物である。
本明細書で言及されている出版物、特許及び特許出願はすべて、各個々の出版物、特許または特許出願が、参照により組み込まれることを具体的に且つ個々に示した場合と同じ程度に本明細書に組み入れられる。
本明細書で使用されるとき、用語「1以上のケラチンの量または活性を調節する」は、1以上のケラチン遺伝子または遺伝子産物のmRNA量、タンパク質量または中間径フィラメントの形成活性における変化(たとえば、増加または低下)を指す。
たとえば、ピペリジン、モルフォリン及びピペラジンのような環状アミンに由来する有機塩、ならびにナトリウム、カルシウム、カリウム、マグネシウム、マンガン、鉄、銅、亜鉛、アルミニウム及びリチウムに由来する無機塩が挙げられる。
ケラチンは約30タンパク質のファミリーであり;それらは上皮細胞の細胞質で最も豊富な構造タンパク質であり、それらは10~12nm幅の中間径フィラメント(IF)のネットワークを形成する。ケラチンタンパク質は、IFをコードする遺伝子のI型とII型の亜群に区分けするヒトのゲノムにて約54を番号付ける保存された遺伝子の大きなファミリーによってコードされている。それぞれ1つのポリペプチド鎖をコードする28のI型(K9~K28、K31~K40)及び26のII型(K1~K8、K71~K86)がある。I型タンパク質は、さらに大きく(52~70kDa)、塩基性~中性で(pI約5.4~8.4)あるII型タンパク質よりも小さく(40~64kDa)、さらに酸性(約4.7~6.1)である傾向がある。I型ケラチンはK9~K20を含み、II型はK1~K8を含む。
カンナビノイドは、皮膚を含むヒトの身体全体にわたって細胞にてカンナビノイド受容体を活性化することが知られる化学物質の群である。フィトカンナビノイドは大麻植物に由来するカンナビノイドである。それらは植物から単離することができ、または合成で製造することができる。エンドカンナビノイドはヒトの身体で見いだされる内在性のカンナビノイドである。
(1)R1はNH2、NHR4、及びNR4R5から成る群から選択され、その任意の炭素原子は任意で置換されてもよく;
(2)R2は水素、アリール、アルキル、シクロアルキル、アラルキル、アルケニル、及びアルキニルから成る群から選択され、その任意の炭素原子は任意で置換されてもよく;
(3)R3は水素、ハロゲン、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、及びヘテロアリールから成る群から選択され、その任意の炭素原子は任意で置換されてもよく;
(4)R4及びR5は独立して変化し、且つアリール、アルキル、シクロアルキル、アラルキル、アルケニル、及びアルキニルから成る群から選択され、その任意の炭素原子は任意で置換されてもよい。
(1)R1はNH2、NHR5、及びNR5R6から成る群から選択され、その任意の炭素原子は任意で置換されてもよく;
(2)R2は水素、アリール、アルキル、シクロアルキル、アラルキル、アルケニル、及びアルキニルから成る群から選択され、その任意の炭素原子は任意で置換されてもよく;
(3)R3及びR4は独立して水素、ハロゲン、アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、及びヘテロアリールから成る群から選択され;
(4)R5及びR6は独立してアリール、アルキル、シクロアルキル、アラルキル、アルケニル、及びアルキニルから成る群から選択され;
(5)R2が水素である場合、R3はt-ブチル、ブロモ、メトキシ、または部分式(C-II(a))の部分ではない。
(1)R1及びR2はそれぞれ水素であり;
(2)R3は(W)m-Y-(Z)nであり、その際、(a)WはC5-C12直鎖または分岐鎖のアルキルであり;(b)Yは原子価結合であり;(c)ZはC5-C12アルキルであり;及び(d)m及びnは異なり、且つそれぞれ0または1のいずれかであり;
(3)R6及びR6’はそれぞれメチルであり;
(4)R7はメチルであり;
(5)QはOであり;
(6)環Cの破線はΔ8-9での二重結合を表す。
(1)R1及びR2は、Cl、F、Br、OH、任意で置換されたC1-C10アルキル、任意で置換されたC1-C10アルコキシ、任意で置換されたC2-C4アルケニル、任意で置換されたC2-C4アルキニル、NR10R11、NHCOR10、NHCO2R10、CH2OR10、CONR10R11、CO2R10、CN、CF3、NO2、N3、C1-C3アルキルthio、R10SO、R10SO2、CF3S、及びCF3SO2から成る群から独立して選択される置換基であり;
(2)R3はHまたはC1-C3アルキルであり;
(3)R4及びR5はそれらが連結されるNと一緒になってピペリジン環を形成し、それは4位にてNR10R11、NR10COR11、NR10SO2R11、NHCONR10R11、NR10COOR11;及びCONR10R11から成る群から選択される少なくとも1つの置換基で置換され;
(4)R10及びR11は独立してH及びC1-C10アルキルから選択され;
(5)a及びbはそれぞれ独立して0~5の整数である。
(1)R1及びR2はそれぞれ独立してアリールから選択され;
(2)R3は水素またはアルキルであり;
その際、R1及びR2の少なくとも一方がオルソ位または[--CH-O--]基への連結点に関連した位置で非水素置換基を有する。
(1)R1は(C1-C6)アルキル;非置換のまたは(C1-C6)アルキル基で1回もしくは数回置換される(C3-C7)シクロアルキル;非置換のまたは炭素環上にて(C1-C3)アルキルによって1回もしくは数回置換される(C3-C7)シクロアルキルメチル;非置換のまたはハロゲン原子、(C1-C4)アルキル、(C1-C6)アルコキシ、シアノ、トリフルオロメチルラジカル、トリフルオロメトキシラジカル、S(O)nAlk基、(C1-C3)アルキルカルボニル基、フェニルから独立して選択される置換基によって一置換、二置換または三置換されるフェニル;非置換のまたはハロゲン原子、(C1-C3)アルキル、(C1-C3)アルコキシから独立して選択される置換基によって一置換または二置換されるベンジル;トリフルオロメチルラジカル;非置換のまたはハロゲン原子もしくはイソオキサゾリルで置換されるチエニルを表し;
(2)R2は水素原子または(C1-C3)アルキルを表し;
(3)R3は水素原子または(C1-C5)アルキルを表し;
(4)R4、R5、R6、R7、R8及びR9はそれぞれ独立して水素原子、ハロゲン原子、(C1-C7)アルキル、(C1-C5)アルコキシ、トリフルオロメチルラジカルまたはS(O)nAlk基を表し;
(5)nは0、1または2を表し;
(6)Alkは(C1-C4)アルキルを表す。
(1)Rは、フェニル、チエニル、2-ピリジニル、3-ピリジニル、4-ピリジニル、ピリミジニル、ピラジニル、ピリダジニルまたはトリアジニルを表し、その基は、同一であることができ、もしくはそれとは異なることができる基C1-C3アルキルもしくはアルコキシ、ヒドロキシ、ハロゲン、トリフルオロメチル、トリフルオロメチルチオ、トリフルオロメトキシ、ニトロ、アミノ、モノ-またはジアルキル(C1-C2)-アミノ、モノ-またはジアルキル(C1-C2)-アミド、(C1-C3)-アルコキシカルボニル、カルボキシル、シアノ、カルバモイル及びアセチルに由来する1、2、3または4の置換基Yによって置換されてもよく、または、Rが4-ピリジニルである場合、R4はハロゲン原子またはシアノ、カルバモイル、ホルミル、アセチル、トリフルオロアセチル、フルオロアセチル、プロピオニル、スルファモイル、メタンスルホニル、メチルスルファニルまたは分岐鎖のもしくは非分岐鎖C1-C4アルキル基を表すという条件で、Rはナフチルを表し、そのC1-C4アルキル基は1~3のフルオロ原子またはブロモ、クロロ、ヨード、シアノもしくはヒドロキシの基で置換されてもよく;
(2)R1はフェニルまたはピリジニルを表し、その基は1~4の置換基Yで置換されてもよく、それは同一であることができ、もしくは異なることができ、その際、Yは上述された意味を有し、またはR1は、ピリミジニル、ピラジニル、ピリダジニルもしくはトリアジニルを表し、その基は1もしくは2の置換基Yで置換されてもよく、それは同一であることができ、もしくは異なることができ、またはR1は基(N,O,S)に由来する1または2のヘテロ原子を有する5員環芳香族複素環を表し、そのヘテロ原子は同一であることができ、もしくは異なることができ、その5員環芳香族複素環は同一であることができ、もしくは異なることができる1 2置換基Yで置換されてもよく、またはR1はナフチルを表し;
(3)R2はH、分岐鎖のまたは非分岐鎖のC1-C8アルキル、C3-C8シクロアルキル、C3-C8アルケニル、C5-C8シクロアルケニルを表し、その基はイオウ原子、酸素原子または窒素原子を含有してもよく;
(4)R3は分岐鎖のまたは非分岐鎖のC2-C8アルキル、C1-C8アルコキシ、C5-C8シクロアルキルオキシ、C5-C8シクロアルキル、C5-C8ビシクロアルキル、C6-C10トリシクロアルキル、C3-C8アルケニルC5-C8シクロアルケニルを表し、それらの基は任意で基(O、N、S)に由来する1以上のヘテロ原子を含有してもよく、且つそれらの基はヒドロキシ基もしくは1もしくは2のC1-C3アルキル基もしくは1~3のフルオロ原子によって置換されてもよく、またはR3はベンジルもしくはフェネチル基を表し、その芳香環は、同一であることができ、もしくは異なることができる、基C1-C3アルキルもしくはアルコキシ、ヒドロキシ、ハロゲン、トリフルオロメチル、トリフルオロメチルチオ、トリフルオロメトキシ、ニトロ、アミノ、モノ-もしくはジアルキル(C1-C2)-アミノ、モノ-もしくはジアルキル(C1-C2)-アミド、(C1-C3)-アルキルスルホニル、ジメチルスルフアミド、C1-C3-アルコキシカルボニル、カルボキシル、トリフルオロメチルスルホニル、シアノ、カルバモイル、スルファモイル及びアセチルに由来する1~5の置換基Zで置換されてもよく、またはR3はフェニル基もしくはピリジニル基を表し、その基は1~4の置換基Zで置換され、その際、Zは上記で示されたような意味を有し、またはR3はピリジニル基を表し、または、R4がハロゲン原子もしくはシアノ、カルバモイル、ホルミル、アセチル、トリフルオロアセチル、フルオロアセチル、プロピオニル、スルファモイル、メタンスルホニル、メチルスルファニルもしくはC1-C4アルキル基を表し、そのC1-C4アルキル基が1~3のフルオロ原子もしくはブロモ、クロロ、ヨード、シアノもしくはヒドロキシ基で置換されてもよいという条件でR3はフェニル基を表し、または、R2が水素原子もしくはメチル基を表すという条件でR3は基NR5R6を表し、その際、R5及びR6は同一であり、もしくは異なっており、分岐鎖のもしくは非分岐鎖のC1-C4アルキルを表し、またはR5及びR6はそれらが連結される窒素原子と一緒になって4~10の環原子を有する飽和もしくは不飽和の、単環式もしくは二環式の複素環基を形成し、その複素環基は基(N,O,S)に由来する1もしくは2のヘテロ原子を含有し、そのヘテロ原子は同一であることができ、もしくは異なることができ、その複素環基は、C1-C3アルキル基もしくはヒドロキシ基で置換されてもよく、またはR2及びR3はそれらが連結される窒素原子と一緒になって4~10の環原子を有する飽和もしくは不飽和の複素環基を形成し、その複素環基は基(N,O,S)に由来する1もしくは2のヘテロ原子を含有し、そのヘテロ原子は同一であることができ、もしくは異なることができ、その複素環基はC1-C3アルキル基もしくはヒドロキシ基で置換されてもよく;
(5)R4は水素原子またはハロゲン原子またはシアノ、カルバモイル、ホルミル、アセチル、トリフルオロアセチル、フルオロアセチル、プロピオニル、スルファモイル、メタンスルホニル、メチルスルファニルまたは分岐鎖のまたは非分岐鎖のC1-C4アルキル基を表し、そのC1-C4アルキル基は、1~3のフルオロ原子またはブロモ、クロロ、ヨード、シアノまたはヒドロキシ基で置換されてもよい。
テルペノイドは独力でカンナビノイド活性を有さず、カンナビノイド受容体に結合しないけれども、それはカンナビノイドの活性と相互作用し、それを強化する。一部の実施形態では、方法はさらに、同一のまたは異なる医薬組成物での治療上有効な量のテルペノイドの同時または逐次の投与を含むことができる。
本発明に係る医薬組成物は1以上の賦形剤を含むことができる。皮膚への塗布を対象とする局所組成物での使用に好適であるそのような賦形剤には、保存剤;増粘剤;緩衝液;等張剤;湿潤剤、可溶化剤及び乳化剤;酸性化剤;抗酸化剤;アルカリ化剤;運搬剤;キレート剤;錯化剤;溶媒;懸濁剤または粘度上昇剤;油;透過増強剤;ポリマー;硬化剤;タンパク質;炭水化物;及び増量剤が挙げられるが、これらに限定されない。
以下の出版物はこの参照によって本明細書に組み入れられる。これらの出版物は以下で提供される番号によって本明細書で参照される。出版物のこのリストにおける出版物の包含は本明細書で参照される出版物が従来技術であるという承認として解釈されるべきではない。
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調べた物質は、フィト-カンナビノイド、カンナビジオール(CBD)、カンナビジオール酸(CBDA)、カンナビノール(CBN)、カンナビジオール:カンナビノール(1:0.1μM)、カンナビジオール:カンナビノール(0.1:1μM)、及びカンナビジオール:カンナビノール(1:1μM)であった。
本明細書に記載されている製剤の皮膚への透過は以下の手順に従って測定された:製剤はラブラソール、プロ-ゲル(ポロキサマー407、レシチン、パルミチン酸イソプロピル)だった。製剤を円の中心部に塗布し、外科用メスを用いて皮膚に擦り付ける。皮膚の外層を上に向けて試料をフランツ拡散セルの上に装着する。フランツセルのレセプター媒体はリン酸緩衝液で満たす。セルのキャップを装着し、締める。この構築物を32℃で18時間インキュベータ/シェーカーの中に入れる(図14)。図15は図14の透過実験の結果を示す(◆、6時間;■、9時間;▲、12時間)。
図19は本明細書に記載されている実験結果に従って開発されたモデルの図である。モデルは皮膚における複数の調節系に関与するエンドカンナビノイド及びカンナビノイド受容体を説明している。
1%FBS及び抗生剤/抗真菌剤で補完したDMEM中でINM-501、INM-509、INM-505、INM-506、INM-513(カンナビゲロール(CBG))、INM-517、HU-210((6aR,10aR)-9-(ヒドロキシメチル)-6,6-ジメチル3-(2-メチルオクタン-2-イル)-6H,6aH,7H,10H,10aH-ベンゾ[c]イソクロメン1-オール))、及びSR144528(すべて1μM濃度にて、EchoPharmaceuticals,AT Nijmegen,The Netherlands,Cayman Chemical,Ann Arbor,MI)の単独での存在下、または10及び20ng/ml濃度での同時に加えたヒト組換えTGFβ1を伴った存在下で24穴プレート(1×105個の細胞/ウェル/mL)にてHaCaT細胞及びHFL-1細胞を72時間培養した。細胞培養の上清を取り除き、プロテイナーゼ/ホスファターゼ阻害剤のカクテルで補完した細胞タンパク質抽出緩衝液で細胞を溶解した。細胞タンパク質抽出物(CPE)を遠心分離によって清澄化し、アッセイの前に-80℃で保った。
角化細胞におけるTGFβ1によって誘導されるEMTをヒトE-カドヘリン(E-CDH)及び細胞性フィブロネクチン(FBN-EDA)の発現によって解析した。線維芽細胞の活性化及び分化はαSMAの発現によって判定した。E-CDH、FBN-EDA及びαSMAのタンパク質は、抗ヒトE-CDH、FBN-EDA及びαSMAのマウスモノクローナル抗体を用いたSDS-PAGE及び免疫ブロットによって測定した。HSP90及びβ-チューブリンを負荷対照として使用した。検出は、LI-COR赤外線画像化システム及びIR700/IR800二次抗体(LI-COR Biosciences,Lincoln,NE)によって行った。バンドの密度は、Odysseyソフトウエア2.1(LI-COR Biosciences)を用いて独立して2つの赤外線チャンネルで定量した。結果はタンパク質/β-チューブリン/HSP90の密度比として表す。
Claims (13)
- 表皮水疱症を治療する方法における使用のためのカンナビノールを含む医薬組成物であって、前記方法が、それを必要とする対象の皮膚に治療上有効な量のカンナビノールを局所投与することを含み、その際、前記治療上有効な量は1以上のケラチンの量または活性を調節するのに十分な量である、前記医薬組成物。
- 前記表皮水疱症が単純型表皮水疱症(EBS)である、請求項1に記載の医薬組成物。
- 前記局所投与が、
局所投与される皮膚の有糸分裂で活性がある基底層にてK15のmRNAもしくはタンパク質のレベルを上げる、またはK5もしくはK14のmRNAもしくはタンパク質のレベルを下げるのに十分な量;または
局所投与される皮膚の有糸分裂で活性がある基底層にてK15のmRNAまたはタンパク質のレベルを上げる、且つK5またはK14のmRNAまたはタンパク質のレベルを下げるのに十分な量;または
局所投与される皮膚の有糸分裂で活性がある基底層にてK15のmRNAまたはタンパク質のレベルを上げる、且つK5及びK14のmRNAまたはタンパク質のレベルを下げるのに十分な量
を局所投与することを含む、請求項1または2に記載の医薬組成物。 - 前記局所投与が、創傷治癒及び皮膚再生を促進するのに十分な量;疼痛及び掻痒を軽減するのに十分な量;または感染の発生を低減するのに十分な量を局所投与することを含む、請求項1~3のいずれか1項に記載の医薬組成物。
- 前記医薬組成物がさらに、前記組成物の局所投与用の少なくとも1つの薬学上許容できるキャリアを含む、請求項1~4のいずれか1項に記載の医薬組成物。
- 前記薬学上許容できるキャリアが、ラブラソール(カプリロカプロイルポリオキシ-8-グリセリド)、ポロキサマー407、レシチン及びパルミチン酸イソプロピルから成る群から選択される少なくとも1つの薬学上許容できるキャリアであるか;または
前記薬学上許容できるキャリアが、ラブラソール、ポロキサマー407、レシチン及びパルミチン酸イソプロピルを含む、
請求項5に記載の医薬組成物。 - 前記方法がさらに、前記表皮水疱症を治療するための局所抗炎症剤、局所抗菌剤、局所抗真菌剤、局所ステロイド、及び局所抗酸化剤から成る群から選択される追加の治療上活性がある作用物質を局所投与するステップを含む、請求項1~6のいずれか1項に記載の医薬組成物。
- 前記方法がさらに、治療上有効な量のテルペノイドを局所投与するステップを含み、ここで
i)前記カンナビノールと前記テルペノイドとが単一の医薬組成物で投与されるか;または
ii)前記カンナビノールと前記テルペノイドとが別々に投与される、
請求項7に記載の医薬組成物。 - 前記局所投与が、
(a)皮膚のアンカリング機能を復元すること;
(b)K5及びK14の一方または双方を下方調節すること;
(c)K15を上方調節すること;
(d)E-カドヘリンのTGF-βが誘導する下方調節を救済すること;及び/または
(e)MCP-1の産生を増やすこと
のために十分な量を局所投与することを含む、請求項1~8のいずれか1項に記載の医薬組成物。 - 表皮水疱症を治療するための医薬の製造におけるカンナビノールの使用であって、前記医薬が
(a)1以上のケラチンの量または活性を調節するのに十分な量である治療上有効な量の前記カンナビノールと
(b)前記医薬の局所投与用の少なくとも1つの薬学上許容できるキャリアとを含み、
前記医薬が局所製剤である、
前記使用。 - 前記表皮水疱症が単純型表皮水疱症(EBS)である、請求項10に記載の使用。
- 前記方法が、局所投与によって組織の有糸分裂で活性がある基底層にてK15のmRNAもしくはタンパク質のレベルを上げる、またはK5もしくはK14のmRNAもしくはタンパク質のレベルを下げるのに十分な量を局所投与することを含むか;または
前記方法が、局所投与される組織の有糸分裂で活性がある基底層にてK15のmRNAまたはタンパク質のレベルを上げる、且つK5またはK14のmRNAまたはタンパク質のレベルを下げるのに十分な量を局所投与することを含むか;または
前記方法が、局所投与される組織の有糸分裂で活性がある基底層にてK15のmRNAまたはタンパク質のレベルを上げる、且つK5及びK14のmRNAまたはタンパク質のレベルを下げるのに十分な量を局所投与することを含むか;または
前記方法が、炎症を軽減すること;創傷治癒及び皮膚再生を促進すること;疼痛及び掻痒を軽減すること;または感染の発生を低減することの少なくとも1つを達成するのに十分な量を局所投与することを含む、
請求項10または11に記載の使用。 - 前記医薬が、
ラブラソール(カプリロカプロイルポリオキシ-8-グリセリド)、ポロキサマー407、レシチン及びパルミチン酸イソプロピルから成る群から選択される薬学上許容できるキャリア、または
ラブラソール、ポロキサマー407、レシチン及びパルミチン酸イソプロピルを含む薬学上許容できるキャリア、及び/または
局所抗炎症剤、局所抗菌剤、局所抗真菌剤、局所ステロイド、及び局所抗酸化剤から成る群から選択される追加の治療上活性がある作用物質
を含み、及び/または
治療上有効な量のテルペノイド
をさらに含む、請求項10~12のいずれか1項に記載の使用。
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AU2017260706B2 (en) | 2023-05-11 |
IL262702A (en) | 2018-12-31 |
EP3452036A4 (en) | 2019-11-06 |
EP3452036A1 (en) | 2019-03-13 |
IL262702B (en) | 2022-06-01 |
US12042479B2 (en) | 2024-07-23 |
CN109689045A (zh) | 2019-04-26 |
AU2017260706A1 (en) | 2018-11-22 |
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WO2017190249A1 (en) | 2017-11-09 |
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