JP2022185139A - Tyk2阻害剤、使用およびその製造のための方法 - Google Patents
Tyk2阻害剤、使用およびその製造のための方法 Download PDFInfo
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- 231100000611 venom Toxicity 0.000 description 1
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- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
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- 229940023080 viracept Drugs 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
驚くべきことに今回、以下の式Iの化合物:
およびその薬学的に許容される塩が、好ましい薬物様特性を有する、Tyk2の有効かつ選択的阻害剤であることが見出された。
また、式Iの化合物を生成するための新規合成方法、およびこのような化合物の合成における新規中間体が開示される。このような方法および中間体は、最新技術と比較して、高収率、好ましい物理化学特性、および有毒な試薬または溶媒の使用の低減により、大規模製造に対応することができる。
)、またはその薬学的に許容される塩を提供する。一部の実施形態では、このような化合物は、以下、またはその薬学的に許容される塩を含む:
一部の実施形態では、本発明は、固体形態の化合物1を提供する。一部の実施形態では、本発明は、不純物を実質的に含まない固体形態の化合物1を提供する。本明細書において使用する場合、「不純物を実質的に含まない」という用語は、化合物が、有意な量の異物を含有しないことを意味する。このような異物は、化合物1の調製、および/または単離から生じ得る残留溶媒、または任意の他の不純物を含み得る。ある特定の実施形態では、少なくとも約95重量%の化合物1が存在する。本発明のさらに他の実施形態では、少なくとも約99重量%の化合物1が存在する。
る。HPLCクロマトグラムの総面積に対して、他の実施形態では、化合物1は、約1.0%面積パーセントHPLC以下のいずれか単一の不純物を、ある特定の実施形態では、約0.5面積パーセントHPLC以下のいずれか単一の不純物を含有する。
見出されている。このようなニート結晶形態の化合物1は、本明細書において詳細に記載されている、形態Iの化合物1のメシル酸塩を含む。
るという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、その粉末X線回折パターンにおいて、表1におけるものから選択される4つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、その粉末X線回折パターンにおいて、表1におけるものから選択される5つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、そのX線回折パターンにおいて、表1におけるピークのうちの10個を有するという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、そのX線回折パターンにおいて、表1におけるピークのうちの15個を有するという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、そのX線回折パターンにおいて、表1におけるピークのうちの20個を有するという点で特徴付けられる。一部の実施形態では、形態I’の化合物1は、そのX線回折パターンにおいて、表1におけるピークのうちのすべてを有するという点で特徴付けられる。
2θ度のピークから選択される4つすべてのピークを有するという点で特徴付けられる。
おいて、表2におけるものから選択される4つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態Iの化合物1は、その粉末X線回折パターンにおいて、表2におけるものから選択される5つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態Iの化合物1は、そのX線回折パターンにおいて、表2におけるピークのうちのすべてを有するという点で特徴付けられる。
る。一部の実施形態では、形態IIの化合物1は、その粉末X線回折パターンにおいて、約22.27、約26.45、約26.02、約16.34、および約17.06 2θ度のピークから選択される5つすべてのピークを有するという点で特徴付けられる。
徴付けられる。
実施形態では、形態Vの化合物1は、その粉末X線回折パターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される2つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態Vの化合物1は、その粉末X線回折パターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される3つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態Vの化合物1は、その粉末X線回折パターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される4つまたはそれより多いピークを有するという点で特徴付けられる。一部の実施形態では、形態Vの化合物1は、その粉末X線回折パターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される5つすべてのピークを有するという点で特徴付けられる。
この発明の化合物は、一般的に上述されたものを含み、さらに、本明細書に開示のクラス、サブクラス、および種によって例証される。本明細書において使用する場合、別段指定されていなければ、以下の定義が適用されることになる。この発明の目的のために、元素周期表、CASバージョン、Handbook of Chemistry and Physics、第75版に従って、化学元素を特定する。さらに、有機化学の一般的原理は、その全体の内容が参照により本明細書に組み込まれる、「Organic Chemistry」、Thomas Sorrell、University Science Books、Sausalito:1999年、ならびに「March’s Advanced Organic Chemistry」、第5版、編:Smith, M.B.およびMarch, J.、John Wiley & Sons、New York:2001年に記載されている。
ピオン酸塩、リン酸塩、ピバル酸塩、プロピオン酸塩、ステアリン酸塩、コハク酸塩、硫酸塩、酒石酸塩、チオシアン酸塩、p-トルエンスルホン酸塩、ウンデカン酸塩、吉草酸塩などが挙げられる。
一部の実施形態では、本発明は、式Iの化合物の生成のための合成方法および合成中間体を提供する。
Ph3)4である。一部の実施形態では、アリールカップリングは、エーテル溶媒中で行われる。一部の実施形態では、エーテル溶媒は、THFである。
のアニリンとのアリールアミノ化を含み、それによって、式A-7の中間体が形成される。一部の実施形態では、式A-6aのアニリンは、p-アミノベンゾイルクロリドの対応する式A6-b:
のピロリジンとのアミノ化によって形成される。一部の実施形態では、アリールアミノ化は、パラジウム触媒系によって触媒される。一部の実施形態では、パラジウム触媒系は、Pd2(dba)3およびキサントホスを含む。一部の実施形態では、アリールアミノ化は、有機溶媒中で行われる。一部の実施形態では、有機溶媒は、ジオキサンである。
別の実施形態によれば、本発明は、この発明の化合物またはその薬学的に許容される塩、エステル、もしくはエステルの塩および薬学的に許容される担体、アジュバント、また
はビヒクルを含む組成物を提供する。この発明の組成物における化合物の量は、生体試料または患者において、Tyk2を測定可能に阻害するのに有効であるようなものである。ある特定の実施形態では、この発明の組成物における化合物の量は、生体試料または患者において、Tyk2を測定可能に阻害するのに有効であるようなものである。ある特定の実施形態では、この発明の組成物は、このような組成物を必要とする患者への投与のために製剤化される。一部の実施形態では、この発明の組成物は、患者への経口投与のために製剤化される。
好ましくは、組成物は、経口、腹腔内または静脈内投与される。この発明の組成物の注射用滅菌形態は、水性または油性の懸濁物であってもよい。これらの懸濁物は、好適な分散剤または湿潤剤および懸濁化剤を使用して、当技術分野で公知の技法に従って製剤化されてもよい。注射用滅菌調製物はまた、例えば、1,3-ブタンジオール中の溶液のように、非毒性の非経口で許容される希釈剤または溶媒中の、注射用滅菌溶液または懸濁物であってもよい。用いることのできる許容されるビヒクルおよび溶媒の中には、水、リンガー溶液および等張塩化ナトリウム溶液である。さらに、滅菌の固定油は、従来より、溶媒または懸濁媒体として用いられている。
限定されないが、鉱油、モノステアリン酸ソルビタン、ポリソルベート60、セチルエステルろう、セテアリルアルコール、2-オクチルドデカノール、ベンジルアルコールおよび水が挙げられる。
薬学的使用
本明細書に記載の化合物および組成物は、一般的に、1つまたは複数の酵素のキナーゼ活性の阻害に有用である。一部の実施形態では、本発明の化合物および方法によって阻害されるキナーゼは、TYK2である。
quezら、「A protein kinase in the interferon α/β signaling pathway」、Cell(1992年)70巻:313頁;Stahlら、「Association and activation of Jak-Tyk kinases by CNTF-LIF-OSM-IL-6β
receptor components」、Science(1994年)263巻:92頁;Finbloomら、「IL-10 induces the tyrosine phosphorylation of Tyk2 and Jak1 and the differential assembly of Stat1 and Stat3 complexes in human T cells and monocytes」、J. Immunol.(1995年)155巻:1079頁;Baconら、「Interleukin 12 (IL-12) induces tyrosine phosphorylation of Jak2 and Tyk2: differential use of Janus family kinases by IL-2 and IL-12」、J. Exp. Med.(1995年)181巻:399頁;Welhamら、「Interleukin-13 signal transduction in lymphohemopoietic cells: similarities and differences in signal transduction with interleukin-4 and insulin」、J. Biol. Chem.(1995年)270巻:12286頁;Parhamら、「A receptor for the heterodimeric cytokine IL-23 is composed of IL-12Rβ1 and
a novel cytokine receptor subunit, IL-23R」、J. Immunol.(2002年) 168巻:5699頁。次いで、活性化TYK2は、さらなるシグナル伝達タンパク質、例えば、STAT1、STAT2、STAT4、およびSTAT6を含むSTATファミリーのメンバーのリン酸化に進む。
loci」、Nat. Genet.(2013年)45巻(7号):730~738頁;Remmersら、「Genome-wide association study identifies variants in the MHC class I, IL10, and IL23R-IL12RB2 regions associated with Behcet’s disease」、Nat. Genet.(2010年)42巻:698~702頁。2,622名の乾癬を有する個体のゲノムワイド関連研究は、疾患の感受性とTYK2の間の関連を特定した。Strangeら、「A
genome-wide association study identifies new psoriasis susceptibility loci and an interaction between HLA-C and ERAP1」、Nat. Genet.(2010年)42巻:985~992頁。TYK2のノックアウトまたはチルホスチン阻害は、IL-23誘導およびIL-22誘導の両方の皮膚炎を
有意に低減する。Ishizakiら、「Tyk2 is a therapeutic
target for psoriasis-like skin inflammation」、Intl. Immunol.(2013年)、doi:10.1093/intimm/dxt062。
mucin expression and goblet cell hyperplasia through TYK2/STAT6 pathway」、FASEB J.(2012年)26巻:1~11頁。
Kinase 2 Plays Critical Roles in the Pathogenic CD4 T Cell Responses for the Development of Experimental Autoimmune Encephalomyelitis」、J. Immunol.(2009年)183巻:7539~7546頁。これは、増大したTYK2発現とMS感受性とを結び付ける、以前の研究の確証となる。Banら、「Replication analysis identifies TYK2 as a multiple sclerosis susceptibility factor」、Eur J. Hum. Genet.(2009年)17巻:1309~1313頁。TYK2における機能喪失変異は、減少した脱髄およびニューロンの増加した髄鞘再形成をもたらし、MSおよび他のCNS脱髄障害の処置におけるTYK2阻害剤の役割をさらに示唆する。
t.(2005年)76巻:528~537頁。SLEを有する個体の、罹患していないコホートに対するゲノムワイド関連研究は、TYK2遺伝子座とSLEの間の高度に有意な相関を示した。Grahamら、「Association of NCF2, IKZF1, IRF8, IFIH1, and TYK2 with Systemic
Lupus Erythematosus」、PLoS Genetics(2011年)7巻(10号):e1002341頁。
Lymphoblastic Leukemia」、Cancer Disc.(2013年)3巻(5号):564~577頁。
i.(2010年)30巻(20号):6873~6881頁。
by cytotoxic T lymphocytes and is reversed by JAK inhibition」、Nat. Med.(2014年)20巻:1043~1049頁;Harelら、「Pharmacologic inhibition of JAK-STAT signaling promotes hair growth」、Sci. Adv.(2015年)1巻(9号):e1500973頁。
vitroアッセイとして、活性化したTYK2、またはその変異体のリン酸化活性および/もしくはその後の機能的結果、またはATPase活性のいずれかの阻害を決定するアッセイが挙げられる。代替のin vitroアッセイによって、阻害剤がTYK2に結合する能力が定量される。阻害剤の結合は、結合前の阻害剤を放射性標識し、阻害剤/TYK2複合体を単離し、結合した放射性標識の量を決定することによって、測定され得る。あるいは、阻害剤の結合は、新規阻害剤が、公知の放射性リガンドに結合したTYK2と共にインキュベートされる競合実験を行うことによって決定され得る。TYK2阻害剤をアッセイするのに有用な、代表的なin vitroアッセイおよびin vivoアッセイとして、例えば、 に記載および開示されるものが挙げられ、その各々は、参照によりその全体として本明細書に組み込まれる。この発明において、TYK2またはその変異体の阻害剤として利用される化合物をアッセイするための詳細な条件は、以下の実施例に記載されている。
る特定の実施形態では、本発明は、TYK2媒介性障害を処置するための方法であって、それを必要とする患者に、本発明の化合物、またはその薬学的に許容される組成物を投与するステップを含む、方法を提供する。
関連する。一部の実施形態では、障害は、IL-12シグナル伝達に関連する。一部の実施形態では、障害は、IL-23シグナル伝達に関連する。
処置される特定の状態、または疾患に依存して、その状態を処置するために通常投与される追加の治療剤を、この発明の化合物および組成物と組み合わせて投与することができる。本明細書において使用する場合、特定の疾患、または状態を処置するために通常投与される追加の治療剤は、「処置される疾患、または状態のために適切である」として公知である。
agent);心臓血管疾患を処置するための薬剤、例えば、ベータ遮断薬、ACE阻害剤、利尿薬、ニトレート、カルシウムチャネル遮断薬、およびスタチン;肝臓疾患を処置するための薬剤、例えば、コルチコステロイド、コレスチラミン、インターフェロン、および抗ウイルス剤;血液障害を処置するための薬剤、例えば、コルチコステロイド、抗白血病剤、および増殖因子;薬物動態を延長または改善する薬剤、例えば、シトクロムP450阻害剤(すなわち、代謝分解の阻害剤)およびCYP3A4阻害剤(例えば、ケトコナゾール(ketokenozole)およびリトナビル)、ならびに免疫不全障害を
処置するための薬剤、例えば、ガンマグロブリンが挙げられる。
keran(登録商標))、シクロスポリン(Sandimmune(登録商標))、レフルノミド(Arava(登録商標))および「抗-TNF」剤(例えば、エタネルセプト(Enbrel(登録商標))、インフリキシマブ(Remicade(登録商標))、ゴリムマブ(Simponi(登録商標))、セルトリズマブペゴール(Cimzia(登録商標))およびアダリムマブ(Humira(登録商標)))、「抗IL-1」剤(例えば、アナキンラ(Kineret(登録商標))およびリロナセプト(Arcalyst(登録商標)))、カナキヌマブ(canakinumab)(Ilaris(登録商標))、抗Jak阻害剤(例えば、トファシチニブ)、抗体(例えば、リツキシマブ(Rituxan(登録商標)))、「抗T細胞」剤(例えば、アバタセプト(Orencia(登録商標)))、「抗IL-6」剤(例えば、トシリズマブ(Actemra(登録商標)))、ジクロフェナク、コルチゾン、ヒアルロン酸(Synvisc(登録商標)またはHyalgan(登録商標))、モノクローナル抗体(例えば、タネズマブ)、抗凝固薬(例えば、ヘパリン(Calcinparine(登録商標)またはLiquaemin(登録商標))およびワルファリン(Coumadin(登録商標)))、下痢止め薬(例えば、ジフェノキシレート(Lomotil(登録商標))およびロペラミド(Imodium(登録商標)))、胆汁酸結合剤(例えば、コレスチラミン)、アロセトロン(Lotronex(登録商標))、ルビプロストン(Amitiza(登録商標))、緩下薬(例えば、マグネシアミルク、ポリエチレングリコール(MiraLax(登録商標))、Dulcolax(登録商標)、Correctol(登録商標)およびSenokot(登録商標))、抗コリン作用薬もしくは鎮痙薬(例えば、ジシクロミン(Bentyl(登録商標)))、Singulair(登録商標)、ベータ-2アゴニスト(例えば、アルブテロール(Ventolin(登録商標)HFA、Proventil(登録商標)HFA)、レバルブテロール(Xopenex(登録商標))、メタプロテレノール(Alupent(登録商標))、酢酸ピルブテロール(Maxair(登録商標))、硫酸テルブタリン(Brethaire(登録商標))、キシナホ酸サルメテロール(Serevent(登録商標))およびフォルモテロール(Foradil(登録商標)))、抗コリン作用剤(例えば、臭化イプラトロピウム(Atrovent(登録商標))およびチオトロピウム(Spiriva(登録商標)))、吸入用コルチコステロイド(例えば、ジプロピオン酸ベクロメタゾン(Beclovent(登録商標)、Qvar(登録商標)、およびVanceril(登録商標))、トリアムシノロンアセトニド(Azmacort(登録商標))、モメタゾン(Asthmanex(登録商標))、ブデソニド(Pulmicort(登録商標))、ならびにフルニソリド(Aerobid(登録商標)))、Afviar(登録商標)、Symbicort(登録商標)、Dulera(登録商標)、クロモリンナトリウム(Intal(登録商標))、メチルキサンチン(例えば、テオフィリン(Theo-Dur(登録商標)、Theolair(登録商標)、Slo-bid(登録商標)、Uniphyl(登録商標)、Theo-24(登録商標))およびアミノフィリン)、IgE抗体(例えば、オマリズマブ(Xolair(登録商標)))、ヌクレオシド逆転写酵素阻害剤(例えば、ジドブジン(Retrovir(登録商標))、アバカビル(Ziagen(登録商標))、アバカビル/ラミブジン(Epzicom(登録商標))、アバカビル/ラミブジン/ジドブジン(Trizivir(登録商標))、ジダノシン(Videx(登録商標))、エムトリシタビン(Emtriva(登録商標))、ラミブジン(Epivir(登録商標))、ラミブジン/ジドブジン(Combivir(登録商標))、スタブジン(Zerit(登録商標))、およびザルシタビン(Hivid(登録商標)))、非ヌクレオシド逆転写酵素阻害剤(例えば、デラビルジン(Rescriptor(登録商標))、エファビレンツ(Sustiva(登録商標))、ネビラピン(Viramune(登録商標))およびエトラビリン(Intelence(登録商標)))、ヌクレオチド逆転写酵素阻害剤(例えば、テノホビル(Viread(登録商標)))、プロテアーゼ阻害剤(例えば、アンプレナビル(Agenerase(登録商標))、アタザナビル(Reyataz(登録商標))、ダルナビル(Prezista(登録商標))、ホスアンプレナ
ビル(Lexiva(登録商標))、インジナビル(Crixivan(登録商標))、ロピナビルおよびリトナビル(Kaletra(登録商標))、ネルフィナビル(Viracept(登録商標))、リトナビル(Norvir(登録商標))、サキナビル(Fortovase(登録商標)またはInvirase(登録商標))、ならびにチプラナビル(Aptivus(登録商標)))、侵入阻害剤(例えば、エンフビルチド(Fuzeon(登録商標))およびマラビロク(Selzentry(登録商標)))、インテグラーゼ阻害剤(例えば、ラルテグラビル(Isentress(登録商標))、ドキソルビシン(Hydrodaunorubicin(登録商標))、ビンクリスチン(Oncovin(登録商標))、ボルテゾミブ(Velcade(登録商標))、およびデキサメタゾン(Decadron(登録商標))の、レナリドミド(Revlimid(登録商標))と組み合わせたもの)、またはこれらの任意の組み合わせ(複数可)が挙げられる。
よびクロロキン(Aralen(登録商標)))、シクロホスファミド(Cytoxan(登録商標))、メトトレキサート(Rheumatrex(登録商標))、アザチオプリン(Imuran(登録商標))および抗凝固薬(例えば、ヘパリン(Calcinparine(登録商標)またはLiquaemin(登録商標))およびワルファリン(Coumadin(登録商標)))から選択される1種または複数の追加の治療剤を投与するステップを含む、方法を提供する。
Dur(登録商標)、Theolair(登録商標)、Slo-bid(登録商標)、Uniphyl(登録商標)、Theo-24(登録商標))およびアミノフィリン)、吸入用コルチコステロイド(例えば、プレドニゾン、プレドニゾロン、ジプロピオン酸ベクロメタゾン(Beclovent(登録商標)、Qvar(登録商標)、およびVanceril(登録商標))、トリアムシノロンアセトニド(Azmacort(登録商標))、モメタゾン(Asthmanex(登録商標))、ブデソニド(Pulmicort(登録商標))、フルニソリド(Aerobid(登録商標))、Afviar(登録商標)、Symbicort(登録商標)、およびDulera(登録商標))から選択される1種または複数の追加の治療剤を投与するステップを含む、方法を提供する。
候群、アテローム性動脈硬化症、アディソン病、パーキンソン病、アルツハイマー病、糖尿病、敗血症性ショック、全身性エリテマトーデス(SLE)、関節リウマチ、乾癬性関節炎、若年性関節炎、変形性関節症、慢性特発性血小板減少性紫斑病、ワルデンシュトレームマクログロブリン血症、重症筋無力症、橋本甲状腺炎、アトピー性皮膚炎、変形性関節疾患、白斑、自己免疫性下垂体機能低下症、ギラン-バレー症候群、ベーチェット病、強皮症、菌状息肉腫、急性炎症性応答(例えば、急性呼吸促迫症候群および虚血/再灌流傷害)、ならびにグレーブス病から選択される、方法を提供する。
ー性鼻炎を含む鼻に影響を与える疾患、および自己免疫反応が関与するかまたは自己免疫成分もしくは病因を有する炎症性疾患(自己免疫性血液学的障害(例えば、溶血性貧血、再生不良性貧血、赤芽球ろうおよび特発性血小板減少症)を含む)、全身性エリテマトーデス、関節リウマチ、多発性軟骨炎、強皮症、ウェゲナー肉芽腫症、皮膚筋炎、慢性活動性肝炎、重症筋無力症、スティーブン-ジョンソン症候群、特発性スプルー、自己免疫性炎症性腸疾患(例えば、潰瘍性結腸炎およびクローン病)、内分泌性眼障害、グレーブス病、サルコイドーシス、肺胞炎、慢性過敏性肺臓炎、多発性硬化症、原発性胆汁性肝硬変、ブドウ膜炎(前部および後部)、乾性角結膜炎および春季カタル、間質性肺線維症、乾癬性関節炎および糸球体腎炎(ネフローゼ症候群(例えば、特発性ネフローゼ症候群または微小変化型腎症を含む)を伴うかまたは伴わないもの)、再狭窄、心臓肥大、アテローム性動脈硬化症、心筋梗塞、虚血性発作およびうっ血性心不全、アルツハイマー病、パーキンソン病、筋萎縮性側索硬化症、ハンチントン病、および脳虚血、ならびに外傷、グルタミン酸神経毒性および低酸素症により引き起こされる神経変性疾患から選択される、方法を提供する。
最も好ましくはヒトを意味する。
するココアバター、ポリエチレングリコールまたは坐剤ろうなどの、好適な非刺激性賦形剤または担体と混合することによって調製することができる坐剤である。
用することができる。この速度は、速度制御膜を設けることによって、または化合物をポリマーマトリクスもしくはゲルに分散させることによって、制御することができる。
タミド(Casodex(商標))を含む。「ゴナドレリンアゴニスト」という用語は、本明細書において使用する場合、これらに限定されないが、アバレリクス、ゴセレリンおよび酢酸ゴセレリンを含む。ゴセレリンは、商品名Zoladex(商標)のもとで投与することができる。
シル酸イマチニブ(Gleevec(商標))またはチルホスチン(例えば、チルホスチンA23/RG-50810;AG 99;チルホスチンAG 213;チルホスチンAG 1748;チルホスチンAG 490;チルホスチンB44;チルホスチンB44(+)鏡像異性体;チルホスチンAG 555;AG 494;チルホスチンAG 556、AG957)およびアダホスチン(4-{[(2,5-ジヒドロキシフェニル)メチル]アミノ}-安息香酸アダマンチルエステル;NSC 680410、アダホスチン)を含む;l)受容体型チロシンキナーゼの上皮増殖因子ファミリー(ホモ二量体またはヘテロ二量体としての、EGFR1 ErbB2、ErbB3、ErbB4)およびそれらの変異体の活性を標的化する、低下させるまたは阻害する化合物であり、例えば、上皮増殖因子受容体ファミリーの活性を標的化する、低下させるまたは阻害する化合物は、特に、EGF受容体型チロシンキナーゼファミリー、例えば、EGF受容体、ErbB2、ErbB3およびErbB4のメンバーを阻害するか、またはEGFもしくはEGF関連リガンドに結合する化合物、タンパク質または抗体(例えば、CP 358774、ZD 1839、ZM 105180;トラスツズマブ(Herceptin(商標))、セツキシマブ(Erbitux(商標))、Iressa、Tarceva、OSI-774、Cl-1033、EKB-569、GW-2016、E1.1、E2.4、E2.5、E6.2、E6.4、E2.11、E6.3もしくはE7.6.3、および7H-ピロロ-[2,3-d]ピリミジン誘導体)であり;m)c-Met受容体の活性を標的化する、低下させるまたは阻害する化合物、例えば、c-Metの活性を標的化する、低下させるまたは阻害する化合物、特に、c-Met受容体のキナーゼ活性を阻害する化合物、またはc-Metの細胞外ドメインを標的化するもしくはHGFに結合する抗体、n)1種または複数のJAKファミリーメンバー(JAK1/JAK2/JAK3/TYK2および/または汎JAK)のキナーゼ活性を標的化する、低下させるまたは阻害する化合物(これらに限定されないが、PRT-062070、SB-1578、バリシチニブ、パクリチニブ、モメロチニブ、VX-509、AZD-1480、TG-101348、トファシチニブ、およびルキソリチニブを含む);o)PI3キナーゼ(PI3K)のキナーゼ活性を標的化する、低下させるまたは阻害する化合物(これらに限定されないが、ATU-027、SF-1126、DS-7423、PBI-05204、GSK-2126458、ZSTK-474、ブパルリシブ、ピクトレリシブ、PF-4691502、BYL-719、ダクトリシブ、XL-147、XL-765、およびイデラリシブを含む);ならびにq)ヘッジホッグタンパク質(Hh)またはスムーズンド受容体(SMO)経路のシグナル伝達効果を標的化する、低下させるまたは阻害する化合物(これらに限定されないが、シクロパミン、ビスモデギブ、イトラコナゾール、エリスモデギブ、およびIPI-926(サリデギブ)を含む)を含む。
ームの活性を標的化する、低下させるまたは阻害する化合物を指す。プロテアソームの活性を標的化する、低下させるまたは阻害する化合物として、これらに限定されないが、ボルテゾミブ(Velcade(商標))およびMLN 341が挙げられる。
プを含む、方法を提供する。一部の実施形態では、FLT3阻害剤は、キザルチニブ(AC220)、スタウロスポリン誘導体(例えば、ミドスタウリンまたはレスタウルチニブ)、ソラフェニブ、タンズチニブ、LY-2401401、LS-104、EB-10、ファミチニブ、NOV-110302、NMS-P948、AST-487、G-749、SB-1317、S-209、SC-110219、AKN-028、フェドラチニブ、トザセルチブ、およびスニチニブから選択される。一部の実施形態では、FLT3阻害剤は、キザルチニブ、ミドスタウリン、レスタウルチニブ、ソラフェニブ、およびスニチニブから選択される。
-4阻害剤、FLT-3阻害剤、VEGFR-2 IgGI抗体、Angiozyme(RPI 4610)およびベバシズマブ(Avastin(商標))などのVEGFの化合物、タンパク質またはモノクローナル抗体もまた、含まれる。
;ならびにベータ-2アドレノセプターアゴニスト(例えば、アルブテロール(サルブタモール)、メタプロテレノール、テルブタリン、サルメテロール フェノテロール、プロカテロール、ならびに、特に、フォルモテロールおよびその薬学的に許容される塩)が挙げられる。好適な気管支拡張薬物として、抗コリン作用性化合物または抗ムスカリン化合物、特に、臭化イプラトロピウム、臭化オキシトロピウム、チオトロピウム塩およびCHF 4226(Chiesi)、ならびにグリコピロレートが挙げられる。一部の実施形態では、本発明による化合物または組成物は、同じ組成物中で、または異なる医薬組成物中で、アプレミラストと一緒に投与される。
て投与される場合、2種の活性な薬剤は、同時に、逐次的にまたは互いからある期間以内に、通常、互いから5時間以内に与えられてもよい。
この発明の化合物、またはその医薬組成物はまた、プロテーゼ、人工弁、移植血管、ステントおよびカテーテルなどの埋込み可能な医療デバイスをコーティングするための組成物中に組み込まれてもよい。例えば、血管ステントは、再狭窄(傷害後の血管壁の再狭小化)を克服するために使用されている。しかし、ステントまたは他の埋込み可能なデバイスを使用する患者には、血餅形成または血小板活性化のリスクがある。これらの不要な効果は、デバイスをキナーゼ阻害剤を含む薬学的に許容される組成物でプレコーティングすることによって、防ぐまたは軽減することができる。この発明の化合物でコーティングされた埋込み可能なデバイスが、本発明の別の実施形態である。
Lの溶液を得て、これを次のステップで直接使用した。
応器に滴下添加し、混合物を30分間撹拌し、次いで、濾過した。水溶液を8Lの酢酸エチルで2回抽出し、合わせた有機層をブライン(4L)で洗浄し、無水硫酸ナトリウムで乾燥させ、次いで、50℃にて真空下で濃縮して、粗生成物を得た。この粗生成物を、実施例4からの900gの生成物を用いて、別のバッチからの粗生成物と合わせ、MTBE(34L)で粉砕し、濾過し、次いで、固体を、3.8Lのアセトニトリルと共に20Lの反応器に投入し、室温で1時間撹拌した。MTBE(9.5L)を室温で1時間滴下添加し、さらに1時間撹拌した。固体を濾過によって回収し、室温で乾燥させて、1.1kgの所望の生成物を97%の純度で得た。精製からの母液を蒸発させ、シリカゲルクロマトグラフィーによって精製して(石油エーテル中33から55%の酢酸エチルの勾配)、さらに550gの粗生成物を得て、これをアセトニトリル(500mL)中に溶解させ、MTBE(1500mL)の滴下添加によって沈殿させた。形成された固体を濾過によって回収し、乾燥させて、さらに430gの生成物を100%の純度で得た。
縮して、粗製の酸クロリドを得て、これをさらに精製することなく使用した。ピロリジン(1300g、5当量)およびジクロロメタン(3.5L、5V)を20Lの反応器に投入し、混合物を0℃まで冷却した。ジクロロメタン(3.5L、5V)中の酸クロリドを、0~5℃で反応器に滴下添加した。HPLCによって反応が完了したと決定されたら、水(7L)を添加し、混合物を濾過した。濾過ケークをジクロロメタン(1.4L)および水(2.8L)で洗浄した。水性相を分離し、ジクロロメタン(7L)で抽出し、有機層を合わせ、次いで、ブライン(3.5L)で洗浄し、無水硫酸ナトリウムで乾燥させ、次いで、50℃にて真空下で濃縮して、粗生成物を得た。粗製物を、室温で終夜、n-ヘプタン:ジクロロメタン(5:1、3.5L)中で終夜撹拌し、次いで、濾過によって固体を回収した。濾過ケークをジクロロメタン(1.4L)および水(2.8L)で洗浄し、両濾過ケークを合わせ、次いで、35~40℃で終夜、ジクロロメタン(2.8L)を用いて撹拌し、次いで、15℃まで冷却し、4時間撹拌した。固体を濾過によって回収し、50℃にて真空下で一定重量まで乾燥させ、所望の生成物(660g、99%の純度)を得た。重水素化したアナログ(すなわち、YおよびまたはZがDであるもの)を、対応する重水素化ピロリジンを使用して同じ手順によって調製した。
に配置した。75μLおよび235μLの緩衝液を、それぞれ、各Transwellインサートとレシーバーウェルに添加した。次いで、150rpmで振盪しながら、プレートを37℃で30分間インキュベートした。対照化合物のストック溶液を10mMにてDMSO中で調製し、次いで、DMSOで1mMまで希釈し、続いて、HBSS(10mMのHEPES、pH7.4)でさらに希釈して、化合物作業溶液を得た。試験化合物のストック溶液を10mMにてDMSO中で調製し、次いで、DMSOで1mMまで希釈し、続いて、HBSS(10mMのHEPES、pH7.4、4%のBSA)でさらに希釈して、化合物作業溶液を得た。試験化合物および対照化合物の最終濃度は、5μMであった。頂端側から側底部側方向への薬物輸送速度を決定するために、75μLの化合物作業溶液をフィルターウェル(頂端側の区画)に添加し、235μLのHBSS(10mMのHEPES、pH7.4、または4%のBSA)をレシーバープレート(側底部側の区画)に添加した。側底部側から頂端側方向への薬物輸送速度を決定するために、235μLの化合物作業溶液をレシーバープレート(側底部側の区画)の各ウェルに添加し、75μLのHBSS(10mMのHEPES、pH7.4、または4%のBSA)をフィルターウェル(頂端側の区画)に添加した。アッセイは二連で実施した。6)プレートを37℃で2時間インキュベートした。輸送期間の終わりに、50μLのアリコートを、頂端側および側底部側のウェルから直接取り出し、新たなプレートのウェルに移した。内部標準(IS、100nMのアルプラゾラム、200nMのラベタロールおよび200nMのジクロフェナク)を含有する4容積の冷メタノールを各ウェルに添加した。試料を、3,220gで30分間遠心分離した。100μLの超純水と混合した100μLの上清のアリコートを、LC-MS/MS分析に使用した。7)溶液をTranswellプレートから廃棄した。100μLのLucifer Yellow溶液(HBSS中100μM)および300μLのHBSSを、漏出の決定のために、それぞれ、Transwellインサートとレシーバーの各ウェルに添加した。プレートを、37℃で30分間インキュベートした。頂端側および側底部側のウェルからの80μLのアリコートを固体ブラックプレートに移し、プレートをTecan Infinite M 200(励起/放出波長485nm/530nm)で読み取った。液体画分、頂端側および側底部側の層を、LC-MSによって分析し、Papp(A-B)、Papp(B-A)および回収を決定した。
、それぞれ、1mMと2mMであった。混合物は、37℃で5分間予め温めた。陰性対照試料を、NADPHおよびUDPGA溶液を80μLの超純粋H2Oで置き換えることによって調製した。陰性対照を使用して、化学物質自体の不安定性に起因する誤解要因を排除した。この研究は二連で実施した。400μMの対照化合物または試験化合物溶液2μLを添加して、反応を開始した。この研究では、ジクロフェナクを陽性対照として使用した。試験化合物または対照化合物の最終濃度は、2μMであった。0、15、30、45および60分に、50μLのアリコートを反応溶液から採取した。反応は、指定した時点で、内部標準(IS)(100nMのアルプラゾラム、200nMのイミプラミン、200nMのラベタロールおよび2μMのケトプロフェン)と共に4容積の冷アセトニトリル(またはメタノール)を添加することによって停止させた。試料を、3,220gで40分間遠心分離して、タンパク質を沈殿させた。100μLの水によって希釈した100μLの上清のアリコートを、LC-MS/MS分析に使用した。in vitro半減期、スケールアップ固有クリアランス、および予測肝クリアランスを、標準計算に従って計算した。
分であった。
(項1)
式I:
の化合物またはその薬学的に許容される塩であって、式中、X、Y、およびZのそれぞれは、独立して、水素または重水素である、化合物またはその薬学的に許容される塩。
(項2)
式:
の上記項1に記載の化合物、またはその薬学的に許容される塩。
(項3)
上記項2に記載の化合物のメシル酸塩。
(項4)
上記項2に記載の化合物の遊離塩基。
(項5)
以下:
からなる群より選択される、上記項1に記載の化合物、またはその薬学的に許容される塩。
(項6)
上記項4に記載の化合物のメシル酸塩。
(項7)
固体形態の上記項1に記載の化合物。
(項8)
固体形態の上記項2に記載の化合物。
(項9)
図1に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結晶形態の上記項4に記載の化合物。
(項10)
XRPDパターンにおいて、約6.07、約11.90、約16.62、および約13.95 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項4に記載の化合物。
(項11)
XRPDパターンにおいて、約6.07、約11.90、約16.62、および約13.95 2θ度のピークから選択される2つまたは1つまたはそれより多いピークを有する、結晶形態の上記項4に記載の化合物。
(項12)
XRPDパターンにおいて、約6.07、約11.90、約16.62、および約13.95 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項4に記載の化合物。
(項13)
図2に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結
晶形態の上記項3に記載の化合物。
(項14)
XRPDパターンにおいて、約19.89、約9.17、約16.88、約14.37、および約22.09 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項3に記載の化合物。
(項15)
XRPDパターンにおいて、約19.89、約9.17、約16.88、約14.37、および約22.09 2θ度のピークから選択される2つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項16)
XRPDパターンにおいて、約19.89、約9.17、約16.88、約14.37、および約22.09 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項17)
XRPDパターンにおいて、約19.89、約9.17、約16.88、約14.37、および約22.09 2θ度のピークから選択される4つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項18)
図3に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結晶形態の上記項3に記載の化合物。
(項19)
XRPDパターンにおいて、約22.27、約26.45、約26.02、約16.34、および約17.06 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項3に記載の化合物。
(項20)
XRPDパターンにおいて、約22.27、約26.45、約26.02、約16.34、および約17.06 2θ度のピークから選択される2つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項21)
XRPDパターンにおいて、約22.27、約26.45、約26.02、約16.34、および約17.06 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項22)
図4に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結晶形態の上記項3に記載の化合物。
(項23)
XRPDパターンにおいて、約18.18、約18.56、約16.95、約21.95、および約9.85 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項3に記載の化合物。
(項24)
XRPDパターンにおいて、約18.18、約18.56、約16.95、約21.95、および約9.85 2θ度のピークから選択される2つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項25)
XRPDパターンにおいて、約18.18、約18.56、約16.95、約21.95、および約9.85 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項26)
図5に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結晶形態の上記項3に記載の化合物。
(項27)
XRPDパターンにおいて、約17.79、約12.45、約24.38、約26.00、および約16.28 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項3に記載の化合物。
(項28)
XRPDパターンにおいて、約17.79、約12.45、約24.38、約26.00、および約16.28 2θ度のピークから選択される2つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項29)
XRPDパターンにおいて、約17.79、約12.45、約24.38、約26.00、および約16.28 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項30)
図6に示されるものと実質的に同様の粉末X線回折(XRPD)パターンを有する、結晶形態の上記項3に記載の化合物。
(項31)
XRPDパターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される1つまたは複数のピークを有する、結晶形態の上記項3に記載の化合物。
(項32)
XRPDパターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される2つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項33)
XRPDパターンにおいて、約13.34、約8.80、約11.10、約16.85、および約25.49 2θ度のピークから選択される3つまたはそれより多いピークを有する、結晶形態の上記項3に記載の化合物。
(項34)
Xが重水素である、上記項1に記載の化合物を生成するためのプロセスであって、式:
の化合物を、塩基の存在下で、重水素供給源と接触させるステップを含む、プロセス。
(項35)
式:
の化合物を生成するためのプロセスであって、
式:
の化合物を、酸と接触させるステップを含む、プロセス。
(項36)
式:
の化合物を生成するためのプロセスであって、
式:
の化合物を、式:
の化合物と接触させるステップを含む、プロセス。
(項37)
式:
の化合物を生成するためのプロセスであって、
式:
の化合物を、2,6-ジフルオロフェニル亜鉛シントンと接触させるステップを含む、プロセス。
(項38)
式:
の化合物を生成するためのプロセスであって、
式:
の化合物を、式:
の化合物および還元剤と接触させるステップを含む、プロセス。
(項39)
式:
の化合物を生成するためのプロセスであって、
式:
の化合物を、還元剤と接触させるステップを含む、プロセス。
(項40)
前記還元剤が、DIBAL-Hである、上記項39に記載のプロセス。
(項41)
式:
の化合物を、-70℃から-80℃の間の温度で、前記還元剤と接触させる、上記項40に記載のプロセス。
(項42)
治療有効量の、上記項1から6のいずれか一項に記載の化合物と、薬学的に許容される担体、アジュバント、または希釈剤とを含む、医薬組成物。
(項43)
治療有効量の、上記項3に記載の化合物と、薬学的に許容される担体、アジュバント、または希釈剤とを含む、医薬組成物。
(項44)
患者または生体試料におけるTyk2酵素を阻害する方法であって、前記患者または前記生体試料を、上記項1から6のいずれか一項に記載の化合物と接触させるステップを含む、方法。
(項45)
Tyk2媒介性障害を処置する方法であって、それを必要とする患者に、上記項1から6のいずれか一項に記載の化合物を投与するステップを含む、方法。
(項46)
前記Tyk2媒介性障害が、自己免疫障害、炎症性障害、増殖性障害、内分泌性障害、神経学的障害、または移植に関連する障害から選択される、上記項45に記載の方法。
(項47)
前記障害が、自己免疫障害である、上記項46に記載の方法。
(項48)
前記自己免疫障害が、1型糖尿病、強直性脊椎炎、全身性エリテマトーデス、多発性硬化症、全身性硬化症、乾癬、クローン病、潰瘍性大腸炎、および炎症性腸疾患から選択される、上記項47に記載の方法。
(項49)
前記障害が、炎症性障害である、上記項46に記載の方法。
(項50)
前記炎症性障害が、関節リウマチ、喘息、慢性閉塞性肺疾患、乾癬、クローン病、潰瘍性大腸炎、および炎症性腸疾患から選択される、上記項49に記載の方法。
(項51)
前記障害が、増殖性障害である、上記項46に記載の方法。
(項52)
前記増殖性障害が、血液学的がんである、上記項51に記載の方法。
(項53)
前記増殖性障害が、白血病である、上記項51に記載の方法。
(項54)
前記白血病が、T細胞白血病である、上記項53に記載の方法。
(項55)
前記T細胞白血病が、T細胞急性リンパ芽球性白血病(T-ALL)である、上記項54に記載の方法。
(項56)
前記増殖性障害が、TYK2における1つまたは複数の活性化変異に関連する、上記項51に記載の方法。
(項57)
前記障害が、移植に関連する、上記項46に記載の方法。
(項58)
前記障害が、移植拒絶または移植片対宿主病である、上記項57に記載の方法。
(項59)
前記障害が、内分泌性障害である、上記項46に記載の方法。
(項60)
前記内分泌性障害が、多嚢胞性卵巣症候群、クルゾン症候群、または1型糖尿病である、上記項59に記載の方法。
(項61)
前記障害が、神経学的障害である、上記項46に記載の方法。
(項62)
前記神経学的障害が、アルツハイマー病である、上記項61に記載の方法。
(項63)
前記障害が、I型インターフェロン、IL-10、IL-12、またはIL-23シグナル伝達に関連する、上記項45に記載の方法。
Claims (8)
- 前記還元剤が、DIBAL-Hである、請求項6に記載のプロセス。
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PCT/US2018/021265 WO2018165240A1 (en) | 2017-03-08 | 2018-03-07 | Tyk2 inhibitors, uses, and methods for production thereof |
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CN110582501A (zh) | 2019-12-17 |
TW202321243A (zh) | 2023-06-01 |
WO2018165240A1 (en) | 2018-09-13 |
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US20190337941A1 (en) | 2019-11-07 |
CN110582501B (zh) | 2022-09-23 |
US10336752B2 (en) | 2019-07-02 |
IL269036A (en) | 2019-10-31 |
IL269036B (en) | 2022-11-01 |
EP3592746B1 (en) | 2024-01-24 |
JP2020511438A (ja) | 2020-04-16 |
US20180258086A1 (en) | 2018-09-13 |
AU2018230737B2 (en) | 2022-09-22 |
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