JP7414525B2 - クロファラビンのプロドラッグ - Google Patents
クロファラビンのプロドラッグ Download PDFInfo
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- JP7414525B2 JP7414525B2 JP2019544805A JP2019544805A JP7414525B2 JP 7414525 B2 JP7414525 B2 JP 7414525B2 JP 2019544805 A JP2019544805 A JP 2019544805A JP 2019544805 A JP2019544805 A JP 2019544805A JP 7414525 B2 JP7414525 B2 JP 7414525B2
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- cancer
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Description
本願は、2016年11月3日に出願された米国仮出願第62/417,081号の利益を主張するものであり、法律によって許容される範囲でその全体が参照によりここに援用される。
並びに、R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
本明細書においては、「プロドラッグ」という用語とは、投与後に、化学的または生理学的なプロセス(例えば、プロドラッグが生理的なpHに到達すること、又は酵素作用によって生物的に活性な化合物に変換すること)を介して、インビボで生物学的に活性な化合物を放出する前駆体化合物をいう。プロドラッグ自体は、所望の生物学的活性を欠いているか、又は持っている可能性がある。
II.クロファラビンのプロドラッグ
並びに、R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
1.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(ヒドロキシメチル)オキソラン;
2.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-2-(エトキシカルボニルオキシメチル)-4-フルオロ-オキソラン;
3.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-2-(エトキシカルボニルオキシメチル)-4-フルオロ-オキソラン-3-オール;
4.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-2-(ブチルオキシカルボニルオキシメチル)-4-フルオロ-オキソラン;
5.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-2-(ブチルオキシカルボニルオキシメチル)-4-フルオロ-オキソラン-3-オール;
6.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(2-メチルプロピルオキシカルボニルオキシメチル)オキソラン;
7.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(2-メチルプロピルオキシ-カルボニルオキシメチル)オキソラン-3-オール;
8.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(ペンチルオキシカルボニルオキシメチル)オキソラン;
9.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(ペンチルオキシカルボニルオキシメチル)オキソラン-3-オール;
10.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(ヘキシルオキシカルボニルオキシメチル)オキソラン;
11.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(ヘキシルオキシカルボニルオキシメチル)オキソラン-3-オール;
12.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(ヘプチルオキシカルボニルオキシメチル)オキソラン;
13.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(ヘプチルオキシカルボニルオキシメチル)オキソラン-3-オール;
14.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(3-フェニルプロパノールオキシメチル)オキソラン;
15.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(3-フェニルプロパノールオキシメチル)オキソラン-3-オール;
16.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-2-(3-(3-ピリジル)プロパノールオキシメチル)オキソラン;
17.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-4-フルオロ-2-(3-(3-ピリジル)プロパノールオキシメチル)オキソラン-3-オール;
18.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-2-[(2S)-2-(tert-ブトキシカルボニルアミノ)-プロパノールオキシメチル]-3-tert-ブチルオキシカルボニルオキシ-4-フルオロ-オキソラン;
19.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-2-[(2S)-2-(tert-ブトキシカルボニルアミノ)-プロパノールオキシメチル]-4-フルオロ-オキソラン-3-オール;及び、
20.(2R,3R,4S,5R)-5-(6-アミノ-2-クロロプリン-9-イル)-2-[(2S)-2-アミノプロパノールオキシメチル]-4-フルオロ-オキソラン-3-オール。
III.医薬組成物
R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
IV.癌を抑制する方法
R3及びR4は、それぞれ独立的にアルキル、置換アルキル、アルケニル、置換アルケニル、アルキニル、置換アルキニル、アリール、置換アリール、アリールアルキル、置換アリールアルキル、シクロアルキル、置換シクロアルキル、シクロヘテロアルキル、置換シクロヘテロアルキル、ヘテロアルキル、及び置換ヘテロアルキルからなる群から選択される。
、ナフテルピン(naphterpin)、ナルトグラスチム、ネダプラチン、ネモルビシン(nemorubicin)、ネリドロン酸(neridronic acid)、中性エンドペプチダーゼ、ニルタミド、ニサマイシン(nisamycin)、一酸化窒素モジュレータ、窒素酸化物抗酸化物、ニトルリン(nitrullyn)、ノコダゾール、ノガラマイシン、n-置換ベンズアミド、06-ベンジルグアニン、オクトレオチド、オキセノン(okicenone)、オリゴヌクレオチド、オナプリストン(onapristone)、オンダンセトロン、オラシン(oracin)、経口サイトカインインデューサー、オルマプラチン、オサテロン(osaterone)、オキサリプラチン、オキサウノマイシン(oxaunomycin)、オキシスラン(oxisuran)、パクリタキセル、パクリタキセル類似体、パクリタキセル誘導体、パラウアミン、パルミトイルリゾキシン(palmitoylrhizoxin)、パミドロン酸、パナキシトリオール(panaxytriol)、パノミフェン(panomifene)、パラバクチン、パゼルリプチン(pazelliptine)、ペガスパルガーゼ、ペルデシン、ペリオマイシン(peliomycin)、ペンタムスチン(pentamustine)、ペントサンポリ硫酸ナトリウム、ペントスタチン、ペントロゾール(pentrozole)、硫酸ペプロマイシン、ペルフルブロン(perflubron)、ペルホスファミド(perfosfamide)、ペリリルアルコール、フェナジノマイシン(phenazinomycin)、酢酸フェニル、ホスファターゼ阻害剤、ピシバニール、塩酸ピロカルピン、ピポブロマン、ピポスルファン、ピラルビシン、ピリトレキシム、塩酸ピロキサントロン(piroxantrone hydrochloride)、プラセチンA(placetin A)、プラセチンB、プラスミノーゲン活性化因子阻害剤、白金錯体、白金化合物、白金-トリアミン錯体、プリカマイシン、プロメスタン(plomestane)、ポルフィマーナトリウム、ポルフィロマイシン、プレドニムスチン、塩酸プロカルバジン、プロピルビスアクリドン(propyl bis-acridone)、プロスタグランジンJ2、前立腺癌抗アンドロゲン(prostatic carcinoma antiandrogen)、プロテアソーム阻害剤、プロテインA-ベース免疫モジュレータ(protein A-based immune modulator)、プロテインキナーゼC阻害剤、プロテインチロシンホスファターゼ阻害剤、プリンヌクレオシドホスホリラーゼ阻害剤、ピューロマイシン、塩酸ピューロマイシン、プルプリン(purpurins)、ピラゾフリン(pyrazofurin)、ピラゾロアクリジン(pyrazoloacridine)、ピリドキシル化ヘモグロビンポリオキシエチレン結合体(pyridoxylated hemoglobin polyoxyethylene conjugate)、RAF拮抗薬、ラルチトレキセド(raltitrexed)、ラモセトロン、RASファルネシルプロテイントランスフェラーゼ阻害剤、RAS阻害剤、RAS-GAP阻害剤、脱メチル化レテリプチン(retelliptine demethylated)、レニウムRE186エチドロン酸塩(rhenium RE 186 etidronate)、リゾキシン、リボプリン(riboprine)、リボザイム、RIIレチナミド、RNAi、ログレチミド(rogletimide)、ロヒツキン(rohitukine)、ロムルチド、ロキニメックス(roquinimex)、ルビギノンBl(rubiginone Bl)、ルボキシル(ruboxyl)、サフィンゴール、塩酸サフィンゴール、サイントピン(saintopin)、sarcnu、サルコフィトールA(sarcophytol A)、サルグラモスチム、SDI 1模倣物、セムスチン、老化由来阻害剤1(senescence derived inhibitor 1)、センスオリゴヌクレオチド、シグナル伝達阻害剤、シグナル伝達モジュレータ、シムトラゼン(simtrazene)、単鎖抗原結合性タンパク質、シゾフラン(sizofuran)、ソブゾキサン、ボロカプテートナトリウム(sodium borocaptate)、フェニル酢酸ナトリウム、ソルベロール(solverol)、ソマトメジン結合タンパク質、ソネルミン(sonermin)、スパルホサートナトリウム(sparfosate sodium)、スパルホシン酸(sparfosic acid)、スパルソマイシン、スピカマイシンD(spicamycin D)、塩酸スピロゲルマニウム(spirogermanium hydrochloride)、スピロマスチン(spiromustine)、スピロプラチン(spiroplatin)、スプレノペンチン(splenopentin)、スポンギスタチン1(spongistatin 1)、スクアラミン、幹細胞阻害剤、幹細胞分裂阻害剤、スチピアミド(stipiamide)、ストレプトニグリン、ストレプトゾシン、ストロメライシン阻害剤、スルフィノシン(sulfinosine)、スロフェヌル(sulofenur)、超活性血管作動性腸管ペプチド拮抗薬(superactive vasoactive intestinal peptide antagonist)、スラジスタ(suradista),スラミン、スワインソニン、合成グリコサミノグリカン、タリソマイシン、タリムスチン(tallimustine)、タモキシフェンメチオジド(tamoxifen methiodide)、タウロムスチン(tauromustine)、タザロテン、テコガランナトリウム(tecogalan sodium)、テガフール、テルラピリリウム(tellurapyrylium)、テロメラーゼ阻害剤、塩酸テロキサントロン(teloxantrone hydrochloride)、テモポルフィン、テモゾロミド、テニポシド、テロキシロン(teroxirone)、テストラクトン、テトラクロロデカオキシド(tetrachlorodecaoxide)、テトラゾミン(tetrazomine)、タリブラスチン(thaliblastine)、サリドマイド、チアミプリン(thiamiprine)、チオコラリン(thiocoraline)、チオグアニン、チオテパ、トロンボポエチン、トロンボポエチン模倣物(thrombopoietin mimetic)、チマルファシン(thymalfasin)、チモポエチン受容体作動薬、サイモトリナン(thymotrinan)、甲状腺刺激ホルモン、チアゾフリン、エチルエチオプルプリンすず、チラパザミン(tirapazamine)、二塩化チタノセン、塩酸トポテカン、トプセンチン(topsentin)、トレミフェン、クエン酸トレミフェン、全能性幹細胞因子(totipotent stem cell factor)、翻訳阻害剤、酢酸トレストロン(trestolone acetate)、トレチノイン、トリアセチルウリジン、トリシリビン(triciribine)、リン酸トリシリビン、トリメトレキサート、グルクロン酸トリメトレキサート、トリプトレリン(triptorelin)、トロピセトロン(tropisetron)、塩酸ツブロゾール(tubulozole hydrochloride)、ツロステリド(turosteride)、チロシンキナーゼ阻害剤、チロホスチン、UBC阻害剤、ウベニメクス(ubenimex)、ウラシルマスタード、ウレデパ(uredepa)、尿生殖洞由来増殖阻害因子(urogenital sinus-derived growth inhibitory factor)、ウロキナーゼ受容体拮抗薬、バプレオチド、バリオリンB、ベラレソール(velaresol)、ベラミン(veramine)、ベルディン(verdins)、ベルテポルフィン、硫酸ビンブラスチン、硫酸ビンクリスチン、ビンデシン、硫酸ビンデシン、硫酸ビネピジン(vinepidine sulfate)、硫酸ビグリシネート(vinglycinate sulfate)、硫酸ビネルロシン(vinleurosine sulfate)、ビノレルビン、酒石酸ビノレルビン、硫酸ビノロシジン(vinrosidine sulfate)、ビンキサルチン(vinxaltine)、硫酸ビンゾリジン(vinzolidine sulfate)、ビタキシン(vitaxin)、ボロゾール(vorozole)、ザノテロン(zanoterone)、ゼニプラチン(zeniplatin)、ジラスコルブ(zilascorb)、ジノスタチン、ジノスタチンスチマラマー(zinostatin stimalamer)、又は塩酸ゾルビシン(zorubicin hydrochloride)を含むが、これらに限定されない。いくつかの実施形態では、抗癌剤は、メトトレキサート、タキソール、L‐アスパラギナーゼ、メルカプトプリン、チオグアニン、ヒドロキシウレア、シタラビン、シクロホスファミド、イホスファミド、ニトロソウレア、シスプラチン、カルボプラチン、マイトマイシン、ダカルバジン、プロカルビジン(procarbizine)、トポテカン、ナイトロジェンマスタード、シトキサン、エトポシド、5-フルオロウラシル、BCNU、イリノテカン、カンプトテシン、ブレオマイシン、ドキソルビシン、イダルビシン、ダウノルビシン、ダクチノマイシン、プリカマイシン、ミトキサントロン、アスパラギナーゼ、ビンブラスチン、ビンクリスチン、ビノレルビン、パクリタキセル、及びドセタキセルから選択される。いくつかの実施形態では、抗癌剤は、シスプラチン、オキサリプラチン、カルボプラチン、エルロチニブ、ゲフィチニブ、ラパチニブ、セツキシマブ、ザルツムマブ、ミノツズマブ(minotuzumab)、及びマツズマブから選択されるが、これらに限定されない。
V.実施例
[製造方法]
スキームI.
実施例1
実施例2
実施例3
実施例4
実施例5
実施例6
実施例7
実施例8
実施例9
実施例10
実施例11
Claims (13)
- 下記式I:
- R1が-C(=O) -O-R3である、請求項1に記載の化合物又はその薬学的に許容可能な塩。
- R2がHである、請求項2に記載の化合物又はその薬学的に許容可能な塩。
- R3が、アルキル及びアリールアルキルからなる群から選択される一つである、請求項1~3のいずれか一つに記載の化合物又はその薬学的に許容可能な塩。
- 式Iで表される化合物又はその薬学的に許容可能な塩と、薬学的に許容可能な担体とを含む、医薬組成物であって、
- R1が-C(=O) -O-R3である、請求項5に記載の医薬組成物。
- R2がHである、請求項6に記載の医薬組成物。
- R3が、アルキル及びアリールアルキルからなる群から選択される一つである、請求項5~7のいずれか一つに記載の医薬組成物。
- 癌を治療するための医薬組成物であって、有効量の請求項1に記載の化合物又はその薬学的に許容可能な塩を含む、医薬組成物。
- さらに、抗癌剤を含む、請求項9に記載の医薬組成物。
- 前記抗癌剤が、従来の化学療法剤、標的治療剤、放射線治療剤、及びこれらの混合物からなる群から選択される、請求項10に記載の医薬組成物。
- 前記抗癌剤が、シタラビン、デシタビン、フルダラビン、ゲムシタビン、アザシチジン、カペシタビン、ソラフェニブ、スニチニブ、イダルビシン、ダウノルビシン、ブスルファン、エトポシド、ミトキサントロン、シクロホスファミド、チオペタ、ベンダムスチン、メルファラン、ビンクリスチン、ビノレルビン、エンチノスタット、デキサメタゾン、メトトレキサート、レナリドマイド、トポテカン、テムシロリムス、リツキシマブ、アレムツズマブ、フィルグラスチム、エプラツズマブ、及びサイモグロブリンからなる群から選択される、請求項10に記載の医薬組成物。
- 前記癌が、白血病、リンパ腫、骨髄異形成症候群、乳癌、及び膵臓癌からなる群から選択される、請求項9に記載の医薬組成物。
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US201662417081P | 2016-11-03 | 2016-11-03 | |
US62/417,081 | 2016-11-03 | ||
PCT/US2017/059420 WO2018085307A1 (en) | 2016-11-03 | 2017-11-01 | Prodrugs of clofarabine |
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ES2938859T3 (es) | 2017-05-01 | 2023-04-17 | Gilead Sciences Inc | Una forma cristalina de (S)-2-etilbutilo 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopirrolo[2,1-f][1,2,4]triazin-7-il)-5-ciano-3,4-dihidroxitetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato |
EP3651734A1 (en) | 2017-07-11 | 2020-05-20 | Gilead Sciences, Inc. | Compositions comprising an rna polymerase inhibitor and cyclodextrin for treating viral infections |
MA55200A (fr) * | 2019-03-06 | 2022-01-12 | Glaxosmithkline Ip No 2 Ltd | Composés utiles dans la thérapie du vih |
BR112021025443A2 (pt) * | 2019-06-18 | 2022-02-01 | Taiho Pharmaceutical Co Ltd | Compostos de éster fosfato com esqueleto de pirrolopirimidina ou sal farmaceuticamente aceitável do mesmo, agentes antitumorais e composições farmacêuticas compreendendo os ditos compostos, bem como usos e usos terapêuticos dos mesmos |
JP2023512656A (ja) | 2020-01-27 | 2023-03-28 | ギリアード サイエンシーズ, インコーポレイテッド | SARS CoV-2感染を治療するための方法 |
TWI785528B (zh) | 2020-03-12 | 2022-12-01 | 美商基利科學股份有限公司 | 1’-氰基核苷之製備方法 |
KR20220164784A (ko) | 2020-04-06 | 2022-12-13 | 길리애드 사이언시즈, 인코포레이티드 | 1'-시아노 치환된 카르바뉴클레오시드 유사체의 흡입 제형 |
EP4157272A1 (en) | 2020-05-29 | 2023-04-05 | Gilead Sciences, Inc. | Remdesivir treatment methods |
TWI819321B (zh) | 2020-06-24 | 2023-10-21 | 美商基利科學股份有限公司 | 1'-氰基核苷類似物及其用途 |
TW202228722A (zh) | 2020-08-27 | 2022-08-01 | 美商基利科學股份有限公司 | 用於治療病毒感染之化合物及方法 |
JP7381913B2 (ja) * | 2021-10-13 | 2023-11-16 | ダイキン工業株式会社 | 有害生物防除組成物 |
EP4320128A1 (en) | 2022-03-02 | 2024-02-14 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
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JP2019533727A (ja) | 2019-11-21 |
CA3042671A1 (en) | 2018-05-11 |
CN110325542A (zh) | 2019-10-11 |
EP3529254A1 (en) | 2019-08-28 |
EP3529254B1 (en) | 2023-02-22 |
WO2018085307A1 (en) | 2018-05-11 |
US11021510B2 (en) | 2021-06-01 |
EP3529254A4 (en) | 2020-08-19 |
US20200095272A1 (en) | 2020-03-26 |
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