JP6817288B2 - 新規な連結体及び生体分子と薬物との特異的共役におけるその使用 - Google Patents
新規な連結体及び生体分子と薬物との特異的共役におけるその使用 Download PDFInfo
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Description
「アルキル」とは、直鎖状又は分岐でもよい、鎖中に1〜8の炭素原子を有する脂肪族炭化水素基を意味する。「分岐」とは、直鎖状のアルキル基に1つ又は複数の低級アルキル、例えば、メチル、エチル、又はプロピル基が結合していることを指す。アルキル基の具体例としては、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、t−ブチル、n−ペンチル、3−ペンチル、オクチル、ノニル、デシル、シクロペンチル、シクロヘキシル、2,2−ジメチルブチル、2,3−ジメチルブチル、2,2−ジメチルペンチル、2,3−ジメチルペンチル、3,3−ジメチルペンチル、2,3,4−トリメチルペンチル、3−メチルヘキシル、2,2−ジメチルヘキシル、2,4−ジメチルヘキシル、2,5−ジメチルヘキシル、3,5−ジメチルヘキシル、2,4−ジメチルペンチル、2−メチルヘプチル、3−メチルヘプチル、n−ヘプチル、イソヘプチル、n−オクチル、及びイソオクチルが含まれる。C1〜C8アルキル基は未置換でもよく、1つ又は複数の置換基(但し、次の置換基に制限されない)で置換されてもよい。前記置換基としては、C1〜C8アルキル、−O−(C1〜C8のアルキル)、アリール、−C(O)R’、−OC(O)R’、−C(O)OR’、−C(O)NH2、−C(O)NHR’、−C(O)N(R’)2、−NHC(O)R’、−SR’、−S(O)2R’、−S(O)R’、−OH、−ハロゲン、−N3、−NH2、−NH(R’)、−N(R’)2、及び−CNが挙げられ、尚、R’はそれぞれ独立にC1〜C8アルキル及びアリールから選択される。
本発明の細胞結合分子に対する薬剤の共役体の調製と同様に、架橋連結体を得る合成経路を図1〜15に示す。架橋連結体は、2つの要素を有する:a)2,3−ジ置換コハク酸基;又は2−モノ置換若しくは2,3−ジ置換フマル基;又は2−モノ置換若しくは2,3−二置換マレイン酸である置換基であり、一対のチオールと反応してチオエーテル結合を形成することができる;及びb)薬剤と反応することが可能な基、これらに限定されないが、ジスルフィド、マレイミド、ハロアセチル、アルデヒド、ケトン、アジド、アミン、アルコキシアミン、ヒドラジド、エテンスルホニル、アシルハライド(酸性ハロゲン化物)、アクリル(アクリロイル)、及び/又は酸無水物基等である。2,3−ジ置換コハク酸基;又は2−モノ置換若しくは2,3−ジ置換フマル基;又は2−モノ置換若しくは2,3−二置換マレイン酸の架橋置換基は、これらの2,3−ジ置換コハク酸、又は2−モノ置換若しくは2,3−ジ置換フマル酸若しくはマレイン酸と、アミド、エステル、又はチオエステル結合を形成するためのアミン、アルコール、チオール基とを直接縮合することにより導入することができる。これらの架橋連結体の合成は、図1、3、4、5、6、7、10、11、12、13、14、及び15に例示されている。
は、細胞結合剤の一対の硫黄原子と反応することができる。前記硫黄原子として好ましくは、還元剤、例えば、ジチオトレイトール(DTT)、ジチオエリスリトール(DTE)、L−グルタチオン(GSH)及びトリス(2−カルボキシエチル)ホスフィン(TCEP)、又は/並びにβメルカプトエタノール(β−ME、2−ME)により、細胞結合剤の鎖間ジスルフィド結合から還元されたチオールの対である。
本発明の共役体及び修飾された細胞結合分子を構成する細胞結合分子は、治療的に又は他の生物学的に修飾されようとする細胞群の残基と結合、複合化、又は反応する、現在知られている、あるいは判明する如何なる分子でもよい。
、ウステキヌマブ(Ustekinumab)(別名:Stelara、抗IL−12、IL−23抗体)、バパリキシマブ(Vapaliximab)(抗AOC3(VAP−1)抗体)、ベドリズマブ(Vedolizumab)、(抗インテグリンα4β7抗体)、ベルツズマブ(抗CD20抗体)、ベパリモマブ(Vepalimomab)(抗AOC3(VAP−1)抗体)、ビシリズマブ(別名:Nuvion、抗CD3抗体)、ビタキシン(抗血管新生インテグリンavb3抗体)、ボロシキシマブ(Volociximab)(抗インテグリンα5β1)、ボツムマブ(Votumumab)(別名:HumaSPECT、抗腫瘍抗原CTAA16.88抗体)、ザルツムマブ(別名:HuMax-EGFr、(抗EGFR抗体)、ザノリムマブ(別名:HuMax-CD4、抗CD4抗体)、ジラリムマブ(Ziralimumab)(抗CD147(基本免疫グロブリン)抗体)、ゾリモマブ(zolimomab)(抗CD5抗体)、エタネルセプト(登録商標「Enbrel」)、アレファセプト(Alefacept)(登録商標「Amevive」)、アバタセプト(登録商標「Orencia」)、リロナセプト(Rilonacept)(Arcalyst)、14F7[抗IRP−2(鉄調節タンパク質2)抗体]、14G2a(Nat.Cancer Inst.から黒色腫及び固形腫瘍のための抗ガングリオシドGD2抗体)、J591(Weill Cornell Medical Schoolから前立腺癌を治療するための抗PSMA抗体、)、225.28S[黒色腫のための抗HMW−MAA(高分子量黒色腫関連抗原)抗体、Sorin Radiofarmaci S.R.L.(ミラノ、イタリア)]、COL−1(Nat. Cancer Inst.から大腸癌及び胃癌のための抗CEACAM3抗体、CGM1)、CYT−356(登録商標「Oncoltad」、前立腺癌)、HNK20(Ora Vax Inc.からRSウイルスのための)、ImmuRAIT(IMMUNOMEDICSから非ホジキンリンパ腫のための)、Lym−1(抗HLA−DR10抗体、Peregrine Pharmから腫瘍のため)、MAK−195F[Abbott/Knollから敗血症、毒素ショックのための抗TNF(腫瘍壊死因子;TNFA、TNF−α;TNFSF2)抗体]、MEDI−500[別名:T10B9、MedImmune Incから移植片対宿主病のための抗CD3抗体、TRαβ(T細胞受容体α/β)、]、RING SCAN[Neoprobe Corp.から乳癌、結腸癌及び結腸直腸癌のための抗TAG72(腫瘍関連糖タンパク質72)抗体)]、Avicidin(抗EPCAM(上皮細胞接着分子)抗体)、抗TACSTD1(腫瘍関連カルシウムシグナルトランスデューサー1)抗体、抗GA733−2(胃腸腫瘍関連タンパク質2)抗体、抗EGP−2(上皮糖タンパク質2)抗体;抗KSA抗体;KS1/4抗原;M4S;腫瘍抗原17−1A;NeoRx Corp.から結腸癌、卵巣癌、前立腺癌、及び非ホジキンリンパ腫のためのCD326;LYMPHOCIDE(IMMUNOMEDICS、NJ)、スマートID10(Protein Design Labs)、Oncolym(Techniclone Inc、CA)、Allomune(BioTransplant、CA)、抗VEGF抗体(ジェネンテック、CA);CEAcide(Immunomedics、NJ)、IMC−1C11(ImClone Systems、NJ)、並びにセツキシマブ(ImClone、NJ)が含まれるが、これらに限られない。
本発明において細胞結合分子と連結することができる薬物は、細胞毒性剤を含む小分子薬物であり、直接又は修飾後に細胞結合分子に連結することができる。ここで、「小分子薬物」は、分子量が例えば100〜1800、より好ましくは120〜1400でもよい有機、無機又は有機金属化合物が広く用いられる。小分子薬物のより良い定義について、WO05058367A2及び米国特許第4,956,303号、並びに他の文献を参考することができ、これらはその全体が参照として組み込まれる。上記薬物には、既知の薬物及び薬物になる可能性のあるものが含まれる。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。R4はOH、H、又は式(I)で定義されるR1若しくはR3である。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。
X1、X2、R1、R2、M1、及びM2は、式(I)及び(II)で定義されているものと同じである。
X1、X2、R1、及びR2は、式(I)及び(II)で定義されているものと同じである。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。加えて、R1及び/又はR2は不存在でもよい。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。加えて、R1及び/又はR2は不存在でもよい。
X1、X2、R1、R2、及びR3は、式(I)及び(II)で定義されているものと同じである。加えて、R1及び/又はR2は不存在でもよい。
塩化メチレン(2.5mL)中のN−Bocアミノ酸(1.0mmol)に、トリフルオロ酢酸(1.0mL)を添加した。室温で1〜3時間撹拌した後、反応混合物を減圧濃縮した。トルエンとの共蒸発により、脱保護された生成物が得られ、これを更に精製することなく使用した。
細胞毒性アッセイのため細胞株として、ヒト白血病細胞株HL−60、ヒト胃癌細胞株NCI−N78、ヒト浸潤性腺管癌細胞株BT−474、及びヒト卵巣癌細胞株SKOV3を使用した。HL−60、NCI−N87、及びBT−47細胞のために、これらの細胞を10%FBS含有RPMI−1640で培養した。SKOV3細胞については、10%FBS含有マッコイの5A培地で培養した。アッセイを実行するために、細胞(180μl、6000細胞)を96ウェルプレートのウェルにそれぞれ加え、37℃、5%CO2で24時間インキュベートした。次いで、適切な細胞培養培地(総量、0.2mL)中で、細胞を種々の濃度の試験用化合物(20μl)で処理した。コントロールウェルは、細胞と培地を含むが、試験化合物を欠いている。プレートを37℃、5%CO2で120時間インキュベートした。MTT(5mg/ml)をウェル(20μl)に添加し、プレートを37℃で1.5時間インキュベートした。その後、培地を注意深く除去し、DMSO(180μl)を加えた。15分間振とうした後、620nmの基準フィルタを用いて490nmと570nmで吸光度を測定した。阻害率%は次の式に従って計算された:阻害率抑%=[1−(分析値−ブランク)/(コントロール−ブランク)]×100
T−DM1と共役体(127)、(129)、及び(142)のインビボ有効性を、ヒト胃癌N−87細胞株腫瘍異種移植モデルにおいて評価した。5週齢の雌BALB/cヌードマウス(30匹)に、0.1mLの無血清培地中のN−87癌腫細胞(5×106細胞/マウス)を右肩下の領域に皮下接種した。腫瘍を8日間、133mm3の平均サイズまで増殖させた。次いで、動物を無作為に5群に分けた(群あたり6匹の動物)。第1群のマウスは対照群として、リン酸緩衝食塩水ビヒクルで処理した。残りの3つの群は、静脈内投与された3mg/kgの用量で、それぞれ共役体(127)、(129)、(142),及びT−DM1で処置した。腫瘍の三次元を4日ごとに測定し、腫瘍容積を式:腫瘍体積=1/2(長さ×幅×高さ)を用いて計算した。動物の体重も同時に測定した。以下の基準の1つに該当する場合、マウスを屠殺した:(1)前処理重量から20%以上の体重減少、(2)1500mm3より大きい腫瘍体積、(3)食物及び水に到達するにはあまりにも元気がない、又は(4)皮膚壊死。腫瘍が触診できなかった場合、マウスは腫瘍がないと判断した。
Claims (29)
- 細胞結合剤と薬物とを共役させるための、式(I)の架橋連結体化合物:
式中、
は、任意の単結合を表す;
は、単結合又は二重結合を表す;
が単結合を表す場合、U及びU’の両方がHではなく;
が二重結合を表す場合、U又はU’のいずれかがHであることができるが、同時にHではない;
2,3−ジ置換コハク酸基、又は2−モノ置換若しくは2,3−ジ置換フマル基、又は2−モノ置換若しくは2,3−二置換マレイン酸であり得る成分
は、細胞結合剤の一対の硫黄原子と反応することができる;前記硫黄原子は、ジチオトレイトール(DTT)、ジチオエリスリトール(DTE)、L−グルタチオン(GSH)及びトリス(2−カルボキシエチル)ホスフィン(TCEP)、又は/並びにβメルカプトエタノール(β−ME、2−ME)を含む還元剤により、細胞結合剤の鎖間ジスルフィド結合から還元されたチオールの対である;
U及びU’は、チオールによって置換されていてもよい同一又は異なる脱離基を表し、そのような脱離基は、ハロゲン化物(フッ化物、塩化物、臭化物、及びヨウ化物)、メタンスルホニル(メシル)、p−トルエンスルホニル(トシル)、トリフルオロメチルスルホニル(トリフラート)、トリフルオロメチルスルホネート、ニトロフェノール、N−ヒドロキシスクシンイミド(NHS)、フェノール;ジニトロフェノール;ペンタフルオロフェノール、テトラフルオロフェノール、ジフルオロフェノール、モノフルオロフェノール、ペンタクロロフェノール、イミダゾール、ジクロロフェノール、テトラクロロフェノール、1−ヒドロキシベンゾトリアゾール、2−エチル−5−フェニルイソオキサゾリウム−3’−スルホネート、又はミツノブ反応のための縮合試薬により生成した中間体分子である。
R1及びR2は、同じか又は異なり、且つ、不存在、炭素数1〜6の直鎖状アルキル、炭素数3〜6の分岐若しくはシクロアルキル、直鎖、分岐若しくはシクロアルケニル若しくはアルキニル、炭素数1〜6のエステル、エーテル若しくはアミド、構造式(OCH2CH2)pである(p;0〜約1000の整数)ポリエチレンオキシ単位、若しくは構造式(OCH2(CH3)CH2)pである(p;0〜約1000の整数)ポリプロピレンオキシ単位、又はこれらの組み合わせであり;
X1及びX2は、NH、N(R3)、O、S、又はCH2から独立して選択され;R3はH、炭素数1〜6の直鎖アルキル、炭素数3〜6の分枝若しくはシクロアルキル、直鎖、分岐若しくはシクロアルケニル若しくはアルキニル、炭素数1〜6のエステル、エーテル若しくはアミド、若しくは構造式(OCH2CH2)pである(p;0〜約1000の整数)ポリエチレンオキシ単位、又はそれらの組み合わせであり;
Z1及びZ2は、ジスルフィド、チオエーテル、チオエステル、ペプチド、ヒドラゾン、エーテル、エステル、カルバメート、カーボネート、アミン(二級、三級若しくは四級)、イミン、シクロヘテロアルカン、ヘテロ芳香環、アルコキシム、又はアミド結合を形成するために細胞毒性剤と反応することができる同一又は異なる官能基であり;前記官能基Z1及びZ2は、以下に示され:
式中、X1はF、Cl、Br、I、又はLv3であり;X2はO、NH、N(R1)、又はCH2であり;R5及びR3は、H、R1、芳香環、ヘテロ芳香環、又は1個若しくは数個のH原子が独立に、−R1、−ハロゲン、−OR1、−SR1、−NR1R2、−NO2、−S(O)R1、−S(O)2R1若しくは−COOR1で置換された芳香族基であり;Lv3はニトロフェノール;N−ヒドロキシスクシンイミド(NHS);フェノール;ジニトロフェノール;ペンタフルオロフェノール;テトラフルオロフェノール;ジフルオロフェノール;モノフルオロフェノール;ペンタクロロフェノール;トリフラート;イミダゾール;ジクロロフェノール;テトラクロロフェノール;1−ヒドロキシベンゾトリアゾール;トシレート;メシレート;2−エチル−5−フェニルイソキサゾリウム−3’−スルホネート、自己若しくは他の酸無水物とで形成された酸無水物(無水酢酸、無水ギ酸を含む。);又はペプチドカップリング反応のための、若しくはミツノブ反応のための縮合試薬により生成する中間体から選択される脱離基である。 - 細胞結合剤及び薬物が請求項1記載の化合物と反応して式(II)となる、請求項1に記載の化合物:
式中、
Cbは、細胞結合剤から選択され;前記共役可能なチオール原子は、一般的に、ジチオスレイトール(DTT)、ジチオエリスリトール(DTE)、L−グルタチオン(GSH)及びトリス(2−カルボキシエチル)ホスフィン(TCEP)、並びに/又はβメルカプトエタノール(β−ME、2−ME)による細胞結合分子上の一対のジスルフィド結合の還元から生成することができる;
「Drug1」及び「Drug2」は、アルキル、アルキレン、アルケニレン、アルキニレン、エーテル、ポリオキシアルキレン、エステル、アミン、イミン、ポリアミン、ヒドラジン、ヒドラゾン、アミド、尿素、セミカルバジド、カルバジド、アルコキシアミン、ウレタン、アミノ酸、ペプチド、アシルオキシルアミン、ヒドロキサム酸、ジスルフィド、チオエーテル、チオエステル、カルバメート、カーボネート、複素環、ヘテロアルキル、ヘテロ芳香環、若しくはアルコキシム結合、又はその組み合わせによって、架橋連結体を介して前記細胞結合剤と連結した、同一の又は異なる細胞毒性剤を表し;
nは1〜30であり;
R1、R2、X1、及びX2は、前述の請求項1に記載のものと同じである。 - 請求項2及び4の式(II)及び(IV)において、Drug1及びDrug2が、同一であるか又は以下から独立に選択されている、請求項2又は4に記載の化合物:
1)化学療法剤:a)アルキル化剤:ナイトロジェンマスタード:クロラムブシル、クロルナファジン、シクロホスファミド、ダカルバジン、エストラムスチン、イホスファミド、メクロレタミン、塩酸メクロレタミンオキサイド、マンノムスチン、ミトブロニトール、メルファラン、ピポブロマン、ノベンビチン、フェネステリン、プレドニムスチン、チオテパ、トロホスファミド、ウラシルマスタード;CC−1065(アドゼレシン、カルゼレシン及びビゼレシンの合成類似体を含む。);デュオカルマイシン(合成類似体、KW−2189及びCBI−TMIを含む。);ベンゾジアゼピン二量体(ピロロベンゾジアゼピン(PBD)又はトマイマイシン、インドリノベンゾジアゼピン類、イミダゾベンゾチアヂアゼピン類、又はオキサゾリジノベンゾジアゼピン類の二量体を含む。);ニトロソ尿素化合物:(カルムスチン、ロムスチン、クロロゾトシン、フォテムスチン、ニムスチン、ラニムスチン);アルキルスルホネート(ブスルファン、トレオスルファン、イムプロスルファン及びピポスルファン);トリアゼン(ダカルバジン);白金含有化合物:(カルボプラチン、シスプラチン、オキサリプラチン);アジリジン類、ベンゾドパ、カルボクオン、メツレドパ、及びウレドパ;エチレンイミン類、並びにアルトレタミン、トリエチレンメラミン、トリエチレンホスホルアミド及びトリエチレンチオホスホルアミンを含むメチラメラミン類を含む;b)植物アルカロイド:ビンカアルカロイド類:(ビンクリスチン、ビンブラスチン、ビンデシン、ビノレルビン、ナベルビン); タキソイド類:(パクリタキセル、ドセタキセル);及びこれらの類似体、メイタンシノイド類(DM1、DM2、DM3、DM4、メイタンシン、アンサマイトシン)及びこれらの類似体、クリプトフィシン類(特に、クリプトフィシン1及びクリプトフィシン8);エポチロン類、エリュテロビン類、ディスコデルモライド、ブリオスタチン類、ドロスタチン類、オーリスタチン類、チューブリシン類、セファロスタチン類;パンクラチスタチン;サルコジクチイン;スポンジスタチン;c)DNAトポイソメラーゼ阻害剤:[エピポドフィリン類:(9−アミノカンプトテシン、カンプトテシン、クリスナトール、ダウノマイシン、エトポシド、リン酸エトポシド、イリノテカン、ミトキサントロン、ノバントロン、レチノイン酸(レチノール類)、テニポシド、トポテカン、9−ニトロカンプトテシン(RFS 2000);マイトマイシン類:(マイトマイシンC))];d)代謝拮抗剤:{[抗葉酸:ジヒドロ葉酸レダクターゼ阻害剤:(メトトレキサート、トリメトレキサート、デノプテリン、プテロプテリン、アミノプテリン(4−アミノプテロイン酸)、又はその他の葉酸類似体);IMPデヒドロゲナーゼ阻害剤(ミコフェノール酸、チアゾフリン、リバビリン、EICAR);リボヌクレオチド還元酵素阻害薬(ヒドロキシウレア、デフェロキサミン)];[ピリミジン類似体:ウラシル類似体(アンシタビン、アザシチジン、6−アザウリジン、カペシタビン(ゼローダ)、カルモフール、シタラビン、ジデオキシウリジン、ドキシフルリジン、エノシタビン、5−フルオロウラシル、フロクスウリジン、ラルチトレキセド(トミュデックス));シトシン類似体:(シタラビン、シトシンアラビノシド、フルダラビン);プリン類似体:(アザチオプリン、フルダラビン、メルカプトプリン、チアミプリン、チオグアニン)];フォリン酸、葉酸補充剤};e)ホルモン療法剤:{受容体拮抗薬:[抗エストロゲン:(メゲストロール、ラロキシフェン、タモキシフェン);LHRHアゴニスト:(ゴセレリン、酢酸リュープロリド);抗アンドロゲン:(ビカルタミド、フルタミド、カルステロン、プロピオン酸ドロモスタノロン、エピチオスタノール、ゴセレリン、リュープロリド、メピチオスタン、ニルタミド、テストラクトン、トリロスタン、及び他のアンドロゲン阻害剤)];レチノイド類/三角筋:[ビタミンD3類似体:(CB1093、EB1089、KH1060、コレカルシフェロール、エルゴカルシフェロール);光線力学的療法剤:(ベルテポルフィン、フタロシアニン、光増感剤Pc4、デメトキシ−ヒポクレリンA);サイトカイン類:(インターフェロンα、インターフェロンγ、腫瘍壊死因子(TNF)、TNFドメイン含有ヒトタンパク質)]};f)キナーゼ阻害剤:BIBW2992(抗EGFR/Erb2)、イマチニブ、ゲフィチニブ、ペガプタニブ、ソラフェニブ、ダサチニブ、スニチニブ、エルロチニブ、ニロチニブ、ラパチニブ、アキシチニブ、パゾパニブ、バンデタニブ、E7080(抗VEGFR2)、ムブリチニブ、ポナチニブ(AP24534)、バフェチニブ(INNO−406)、ボスチニブ(SKI−606)、カボザンチニブ、ビスモデギブ、イニパリブ、ルキソリチニブ、CYT387、アキシチニブ、チボザニブ、ソラフェニブ、ベバシズマブ、セツキシマブ、トラスツズマブ、ラニビズマブ、パニツムマブ、イスピネシブを含む。;g)抗生物質:エンジイン系抗生物質(カリケアマイシン類、特に、カリケアマイシンγ1、δ1、α1及びβ1;ダイネミシンA及びデオキシダイネミシンを含むダイネミシン;エスペラミシン、ケダルシジン、C−1027、マズロペプチン、並びにネオカルジノスタチンクロモフォア及び関連する色素タンパク質エンジイン抗生物質クロモフォア、アクラシノマイシン類、アクチノマイシン、アンスラマイシン、アザセリン、ブレオマイシン類、カクチノマイシン(cactinomycin)、カラビシン(carabicin)、カルミノマイシン、カルジノフィリン;クロモマイシン類、ダクチノマイシン、ダウノルビシン、デトルビシン、6−ジアゾ−5−オキソ−L−ノルロイシン、ドキソルビシン、モルホリノ−ドキソルビシン、シアノモルホリノ−ドキソルビシン、2−ピロリノ−ドキソルビシン及びデオキシドキソルビシン、エピルビシン、イダルビシン、マルセロマイシン、マイトマイシン類、ミコフェノール酸、ノガラマイシン、オリボマイシン類、ペプロマイシン、ポトフィロマイシン、ピューロマイシン、クエラマイシン、ロドルビシン、ストレプトニグリン、ストレプトゾシン、ツベルシジン、ウベニメクス、ジノスタチン、ゾルビシンを含む。;f)その他のカテゴリー:ポリケチド(アセトゲニン類)、特にブラタシン及びブラタシノン;ゲムシタビン、エポキソミシン類(カルフィルゾミブを含む。)、ボルテゾミブ、サリドマイド、レナリドミド、ポマリドマイド、トセドスタット、ザイブレスタット、PLX4032、STA−9090、スチムバックス(Stimuvax)、アロベクチン−7、ザイゲバ、プロベンジ、エルボイ、イソプレニル化阻害剤(ロバスタチン)、ドーパミン作動性神経毒(1−メチル−4−フェニルピリジンイオンを含む。)、細胞周期阻害剤(スタウロスポリンを含む。)、アクチノマイシン類(アクチノマイシンD、ダクチノマイシンを含む。)、ブレオマイシン類(ブレオマイシンA2、ブレオマイシンB2、ペプロマイシンを含む。)、アントラサイクリン類(ダウノルビシン、ドキソルビシン(アドリアマイシンを含む。)、イダルビシン、エピルビシン、ピラルビシン、ゾルビシン、ミトキサントロン、MDR阻害剤(ベラパミルを含む。)、Ca2+ATP阻害剤(タプシガルギンを含む。)、ヒストン脱アセチル化酵素阻害剤(ボリノスタット、ロミデプシン、パノビノスタット、バルプロ酸、モセチノスタット(MGCD0103)、ベリノスタット、PCI−24781、エンチノスタット、SB939、レスミノスタット、ギビノスタット、AR−42、CUDC−101、スルフォラファン、トリコスタチンA);タプシガルギン、セレコキシブ、グリタゾン類、エピガロカテキンガレート、ジスルフィラム、サリノスポラミドA、及びアミノグルテチミド、ミトタン、トリロスタン;アセグラトン;アルドホスファミドクリコシドを含む抗副腎薬;アミノレブリン酸;アラビノシド、ベストラブシル;ビサントレン;エダトレキサート;デフォファミン、デメコルシン、ジアジコン、エルフォルニチン(DFMO)、酢酸エリプチニウム、エトクルシド、硝酸ガリウム、ガシトシン、ヒドロキシ尿素;イバンドロネート、レンチナン;ロニダミン;ミトグアゾン;モピダモール;ニトラエリン;ペントスタチン;フェナメット;ピラルビシン;ポドフィリン酸;2−エチルヒドラジド;プロカルバジン;PSK(登録商標);ラゾキサン;リゾキシン;シゾフィラン;スピロゲルマニウム;テニュアゾン酸;トリアジコン;2,2’,2’’−トリクロロトリエチルアミン;トリコテセン類(特に、T2トキシン、ベルカリンA、ロリジンA、及びアングイジン);ウレタン、siRNA、アンチセンス医薬、並びに核酸分解酵素;
2)抗自己免疫疾患薬:シクロスポリン、シクロスポリンA、アザチオプリン、アミノカプロン酸、ブロモクリプチン、クロラムブシル、クロロキン、シクロホスファミド、コルチコイド(ホルモン剤、ベタメタゾン、ブデソニド、フルニソリド、フルチカゾンプロピオン酸エステル、ヒドロコルチゾン、デキサメタゾン、フルオコルトダナゾール、トリアムシノロンアセトニド、ジプロピオン酸ベクロメタゾンを含む。)、デヒドロイソアンドロステロン、エタネルセプト、ヒドロキシクロロキン、インフリキシマブ、メロキシカム、メトトレキサート、ミコフェノール酸モフェチル、シロリムス、タクロリムス、プレドニゾン;
3)抗感染薬:a)アミノグリコシド類:アミカシン、アストロマイシン、ゲンタマイシン(ネチルマイシン、シソマイシン、イセパマイシン)、ハイグロマイシン、カナマイシン(アミカシン、アルベカシン、アミノデオキシカナマイシン、ジベカシン、トブラマイシン)、ネオマイシン(ネオマイシンB、パロモマイシン、リボスタマイシン)、ネチルマイシン, スペクチノマイシン、ストレプトマイシン、トブラマイシン、ベルダミシン;b)アンフェニコール類:アジダムフェニコール、クロラムフェニコール、フロルフェニコール、チアンフェニコール;c)アンサマイシン類:ゲルダナマイシン、ハービマイシン;d)カルバペネム類:ビアペネム、ドリペネム、エルタペネム、イミペネム/シラスタチン、メロペネム、パニペネム;e)セフェム類:カルバセフェム(ロラカルベフ)、セファセトリル、セファクロル、セフラジン、セファドロキシル、セファロニウム、セファロリジン、セファロチン又はセファロスポリン、セファレキシン、セファログリシン、セファマンドール、セファピリン、セファトリジン、セファザフル、セファゼドン、セファゾリン、セフブペラゾン、セフカペン、セフダロキシム、セフェピム、セフミノックス、セフォキシチン、セフプロジル、セファロスポリン、セフテゾル、セフロキシム、セフィキシム、セフジニル、セフジトレン、セフェピム、セフェタメト、セフメノキシム、セフォジジム、セフォニシド、セフォペラゾン、セホラニド、セフォタキシム、、セフォチアム、セフォゾプラン、セファレキシン、セフピミゾール、セフピラミド、セフピロム、セフポドキシム、セフプロジル、セフキノム、セフスロジン、セフタジジム、セフテラム、セフチブテン、セフチオレン、セフチゾキシム、セフタジジム、セフトリアキソン、セフロキシム、セファゾリンフラン、セファマイシン(セフォキシチン、セフォテタン、セフメタゾール)、オキサセフェム(フロモキセフ、ラタモキセフ);f)糖ペプチド類:ブレオマイシン、バンコマイシン(オリタバンシン、テラバンシン)、テイコプラニン(ダルババンシン)、ラモプラニン、キュービシン;g)グリシルサイクリン類:チゲサイクリンを含む。;h)β−ラクタマーゼ阻害剤:ペナム(スルバクタム、タゾバクタム)、クラバム(クラブラン酸);i)リンコサミド類:クリンダマイシン、リンコマイシン;j)リポペプチド類:ダプトマイシン、A54145、カルシウム依存性抗生物質(CDA);k)マクロライド類:アジスロマイシン、セスロマイシン、クラリスロマイシン、ジリスロマイシン、エリスロマイシン、フルリスロマイシン、ジョサマイシン、ケトライド(テリスロマイシン、エセスロマイシン)、ミデカマイシン、ミオカマイシン、オレアンドマイシン、リファマイシン(リファンピシンン、リファンピン、リファブチン、リファペンチン)、ロキタマイシン、ロキシスロマイシン、スペクチノマイシン、スピラマイシン、タクロリムス(FK506)、トロレアンドマイシン、テリスロマイシンン;l)モノバクタム類:アズトレオナム、チゲモナム;M)オキサゾリジノン類:リネゾリド;N)ペニシリン類:アモキシシリン、アンピシリン(ピバンピシリン、ヘタシリン、バカンピシリン、メタンピシリン、タランピシリン)、アジドシリン、アズロシリン、ペニシリン、ベンザチンペニシリン、フェノキシベンザチンペニシリン、クロメトシリン、プロカインペニシリン、カルベニシリン(カリンダシリン)、クロキサシリン、ジクロキサシリン、セファロスポリン、フルクロキサシリン、メシリナム(ピブメシリナム)、メズロシリン、メチシリン、ナフシリン、オキサシリンナトリウム、フェネチシリン、ペニシリン、フェネチシリン、ペニシリン、ピペラシリン、プロピシリン、スルベニシリン、テモシリン、チカルシリン;o)ポリペプチド類:バシトラシン、ポリミキシンE、ポリミキシンB; p)キノロン類:アラトロフロキサシン、バロフロキサシン、シプロフロキサシン、クリナフロキサシン、ダノフロキサシン、ジフロキサシン、エノキサシン、エンロフロキサシン、オフロキサシン、ガレノキサシン、ガチフロキサシン、ゲミフロキサシン、グレパフロキサシン、カノトロバフロキサシン(kanotroafloxacin)、レボフロキサシン、ロメフロキサシン、マルボフロキサシン、モキシフロキサシン、ナジフロキサシン、ノルフロキサシン、オルビフロキサシン、オフロキサシン、ペフロキサシン、トロバフロキサシン、グレパフロキサシン、シタフロキサシン、スパルフロキサシン、テマフロキサシン、トスフロキサシン、トロバフロキサシン;q)ストレプトゾトシン類:プリスチナマイシン、キヌプリスチン/ダルホプリスチン;r)スルホンアミド類:マフェニド、プロントジル、スルファセタミド、スルファメトキサゾール、スルファニルアミド、スルファサラジン、スルファフラゾール、トリメトプリム、トリメトプリム−スルファメトキサゾール(コトリモキサゾール);s)ステロイド系抗菌薬:フシジン酸を含む;t)テトラサイクリン類:ドキシサイクリン、クロルテトラサイクリン、クロモサイクリン、デメクロサイクリン、リメサイクリン、メクロサイクリン、メタサイクリン、ミノサイクリン、オキシテトラサイクリン、ペニメピサイクリン、ロリテトラサイクリン、テトラサイクリン、グリシルサイクリン(チゲサイクリンを含む。);u)他のタイプの抗生物質:アンノナシン、アルスフェナミン、バクトプレノール阻害剤(バシトラシン)、DADAL/AR阻害剤(サイクロセリン)、ジクチオスタチン、ディスコデルモライド、エレウテロビン、エポチロン、エタンブトール、エトポシド、ファロペネム、フシジン酸、フラゾリドン、イソニアジド、ラウリマリド、メトロニダゾール、ムピロシン、マイコラクトン、NAM合成阻害剤(ホスホマイシンを含む。)、ニトロフラントイン、パクリタキセル、プラテンシマイシン、ピラジナミド、キヌプリスチン/ダルホプリスチン、リファンピン(リファンピシン)、タゾバクタムチニダゾール、ウバリシン;
4)抗ウイルス薬:a)侵入/融合阻害剤:アプラビロック、マラビロク、ビクリビロック、gp41(エンフビルチド)、PRO140、CD4(イバリズマブ);b)インテグラーゼ阻害剤:ラルテグラビル、エルビテグラビル、グロボイドナンA;c)成熟阻害剤:ベビリマット、ヴィヴィコン;d)ノイラミニダーゼ阻害剤:オセルタミビル、ザナミビル、ペラミビル;e)ヌクレオシド及びヌクレオチド:アバカビル、アシクロビル、アデフォビル、アムドキソビル、アプリシタビン、ブリブジン、シドフォビル、クレブジン、デキセルブシタビン、ジダノシン(DDI)、エルブシタビン、エムトリシタビン(FTC)、エンテカビル、ファムシクロビル、フルオロウラシル(5−FU)、3’−フルオロ置換2’,3’−デオキシヌクレオシド類似体(3’−フルオロ−2’,3’−ジデオキシチミジン(FLT)及び3’−フルオロ−2’,3’−ジデオキシグアノシン(FLG)を含む。)、ホミビルセン、ガンシクロビル、イドクスウリジン、ラミブジン(3TC)、L−ヌクレオシド(β−L−チミジン、β−L−2’−デオキシシチジンを含む。)、ペンシクロビル、ラシビル、リバビリン、スタンピジン、スタブジンセット(d4T)、タリバビリン(ビラミジン)、テルビブジン、テノホビル、トリフルリジン、バラシクロビル、バルガンシクロビル、ザルシタビン(ddC)、ジドブジン(AZT);f)非ヌクレオシド:アマンタジン、アテビリジン、カプラビリン、ジアリールピリミジン(エトラビリン、リルピビリン)、デラビルジン、ドコサノール、エミビリン、エファビレンツ、ホスカルネット(ホスホリルギ酸)、イミキモド、インターフェロンα、ロビリド、ロデノシン、メチサゾン、ネビラピン、NOV−205、ペグインターフェロンα、ポドフィロトキシン、リファンピシン、リマンタジン、レシキモド(R−848)、トロマンタジン;g)プロテアーゼ阻害剤:アンプレナビル、アタザナビル、ボセプレビル、ダルナビル、ホスアンプレナビル、インジナビル、ロピナビル、ネルフィナビル、プレコナリル、リトナビル、サキナビル、テラプレビル(VX−950)、チプラナビル;H)抗ウイルス薬の他のタイプ:アブザイム、アルビドール、カラノリドA、セラゲニン、シアノビリン−N、DAPY、没食子酸エピガロカテキン(EGCG)、ホスカルネット、グリフィスシン、タリバビリン(ビラミジン)、ヒドロキシカルバミド、KP−1461、プレコナリル、ポートマントー阻害剤、リバビリン、セリシクリブ;
5)3H、11C、14C、18F、32P、35S、64Cu、68Ga、86Y、99Tc、111In、123I、124I、125I、131I、133Xe、177Lu、211At、及び213Biから選択される放射性同位元素(放射性核種);
6)UV光、蛍光光、IR光、近IR光、視覚光を含むある種の光を吸収する能力を有する発色団分子;黄色素胞、赤色素胞、虹色素胞、白色素胞、黒色素胞、青色素胞、及び蛍光体のクラス又はサブクラスであって、前記蛍光体は、光で光を再放射する蛍光性化学物質、視覚的光感受性分子、発光分子、ルミネッセンス分子、ルシフェリン化合物のクラスまたはサブクラス、可視光伝達分子、発光分子、ルミネセンス分子、ルシフェリン化合物;以下の非タンパク質有機蛍光体:キサンテン誘導体(フルオレセイン、ローダミン、オレゴングリーン、エオシン、及びテキサスレッド);シアニン誘導体(シアニン、インドカルボシアニン、オキサカルボシアニン、チアカルボシアニン、及びメロシアニン);スクアレン誘導体及び環置換スクアライン(Seta、SeTau、及びSquare色素を含む);ナフタレン誘導体(ダンシル及びプロダン誘導体);クマリン誘導体;オキサジアゾール誘導体(ピリジルオキサゾール、ニトロベンゾキサジアゾール、及びベンゾオキサジアゾール);アントラセン誘導体(DRAQ5、DRAQ7、及びCyTRAK Orangeを含むアントラキノン類);ピレン誘導体(カスケードブルー等);オキサジン誘導体(ナイルレッド、ナイルブルー、クレシルバイオレット、オキサジン170等)。アクリジン誘導体(プロフラビン、アクリジンオレンジ、アクリジンイエロー等)。アリールメチン誘導体(オーラミン、クリスタルバイオレット、マラカイトグリーン)。テトラピロール誘導体(ポルフィン、フタロシアニン、ビリルビン); 以下の蛍光体化合物の任意の類縁体及び誘導体:CF色素(Biotium)、DRAQ及びCyTRAKプローブ(Bio-Status)、BODIPY(Invitrogen)、Alexa Fluor(Invitrogen)、DyLight Fluor(Thermo Scientific、Pierce)、Atto及びTrancy(Sigma Aldrich)、FluoProbes(Interchim)、Abberior色素(Abberior)、DY及びMegaStokes色素(Dyomics)、SulfoCy色素(Cyandye)、HiLyte Fluor(AnaSpec)、Seta、SeTau及びSquare色素(SETA BioMedicals)、Quasar及びCal Flour色素(Biosearch Technologies)、SureLight色素(APC、RPEPerCP、フィコビリソーム)(Columbia Biosciences)、APC、APCXL、RPE、BPE(Phyco-Biotech)、アロフィコシアニン(APC)、アミノクマリン、APC−Cy7共役体、BODIPY−FL、カスケードブルー、Cy2、Cy3、Cy3.5、Cy3B、Cy5、Cy5.5、Cy7、フルオレセイン、FluorX、ヒドロキシクマリン、リサミンローダミンB、ルシファーイエロー、メトキシクマリン、NBD、Pacific Blue、Pacific Orange、PE−Cy5共役体、PE−Cy7共役体、PerCP、R−フィコエリトリン(PE)、Red613、Seta−555−アジド、Seta−555−DBCO、Seta−555−NHS、Seta−580−NHS、Seta−680−NHS、Seta−780−NHS、Seta−APC−780、Seta−PerCP−680、Seta−R−PE−670、SeTau380−NHS、SeTau405−マレイミド、SeTau405−NHS、SeTau425−NHS、SeTau647−NHS、テキサスレッド、TRITC、TruRed、X−ローダミン、7−AAD(7−アミノアクチノマイシンD、CG選択性)、アクリジンオレンジ、クロモマイシンA3、CyTRAKオレンジ(Biostatus、赤色励起暗)、DAPI、DRAQ5、DRAQ7、エチジウムブロマイド、ヘキスト33258、ヘキスト33342、LDS751、ミスラマイシン、ヨウ化プロピジウム(PI)、SYTOXブルー、SYTOXグリーン、SYTOXオレンジ、チアゾールオレンジ、TO−PRO:シアニン単量体、TOTO−1、TO−PRO−1、TOTO−3、TO−PRO−3、YOseta−1、YOYO−1。細胞研究のために本発明の連結体に連結させることができる蛍光色素は、以下の化合物又はその誘導体から選択される:DCFH(2’7’ジクロロジヒドロ−フルオレセイン、酸化型)、DHR(ジヒドロローダミン123、酸化型、光が酸化を触媒する)、Fluo−3(AMエステル、pH>6)、Fluo−4(AMエステル、pH7.2)、Indo−1(AMエステル、低/高カルシウム(Ca2+))、SNARF(pH6/9)、アロフィコシアニン(APC)、AmCyan1(四量体、Clontech)、AsRed2(四量体、Clontech)、Azamiグリーン(単量体、MBL)、アズライト、B−フィコエリトリン(BPE)、セルリアン、CyPet、DsRed単量体(Clontech)、DsRed2(「RFP」、Clontech)、EBFP、EBFP2、ECFP、EGFP(弱二量体、Clontech)、エメラルド(弱二量体、Invitrogen)、EYFP(弱二量体、Clontech)、GFP(S65A変異体)、GFP(S65C変異体)、GFP(S65L変異体)、GFP(S65T変異体)、GFP(Y66F変異体)、GFP(Y66H変異体)、GFP(Y66W変異体)、GFPuv、HcRed1、J−Red、カチューシャ、Kusabira Orange(単量体、MBL)、mCFP、mCherry、mCitrine、Midriishi Cyan(二量体、MBL)、mKate(TagFP635、単量体、Evrogen)、mKeima−Red(単量体、MBL)、mKO、mOrange、mPlum、mRaspberry、mRFP1(単量体、Tsien Lab)、mStrawberry、mTFP1、mTurquoise2、P3(フィコビリソーム複合体)、Peridinin Chlorophyll(PerCP)、R−フィコエリトリン(RPE)、T−Sapphire、TagCFP(二量体、Evrogen)、TagGFP(二量体、Evrogen)、TagRFP(二量体、Evrogen)、TagYFP(二量体、Evrogen)、tdTomato(タンデム二量体)、トパーズ、TurboFP602(二量体、Evrogen)、TurboFP635(二量体、Evrogen)、TurboGFP(二量体、Evrogen)、TurboRFP(二量体、Evrogen)、TurboYFP635(二量体、Evrogen)、ビーナス、天然型GFP、YPet、Zsグリーン1(四量体、Clontech)、Zsイエロー1(四量体、Clontech)。
7)薬学的に許容される、上記の任意の薬物の塩、酸、又は誘導体。 - 前記「Drug1」及び「Drug2」は発色団であり、検出、モニタリング、又は前記細胞結合分子、及び/又は前記共役体と標的、特に、標的細胞との相互作用及び/又は機能の研究のために使用することができる、請求項2又は4に記載の化合物。
- 前記「Drug1」及び「Drug2」は、哺乳類に投与された場合、細胞結合分子の半減期を延長するために使用されるポリアルキレングリコール又はポリアルキレングリコール類縁体とすることができ、ポリアルキレングリコールは、約10ダルトン〜約200kDaの分子量を有するポリ(エチレングリコール)(PEG)、ポリ(プロピレングリコール)、エチレンオキシド又はプロピレンオキシドの共重合体である、請求項2又は4に記載の化合物。
- 前記「Drug1」及び「Drug2」は、前記共役体を悪性細胞に送達するために、前記共役体が標的コンダクター/ディレクターとして働くことができる、あるいは所望の免疫応答を調節若しくは共刺激するか、又はシグナル伝達経路を変更することもできる、細胞結合リガンド若しくは受容体、又は受容体類似体とすることができる、請求項2又は4に記載の化合物。
- 前記細胞結合リガンド又は受容体が以下から選択される、請求項8に記載の化合物:葉酸誘導体;グルタミン酸尿素誘導体;ソマトスタチン及びその類縁体;芳香族スルホンアミド;下垂体アデニレートシクラーゼ活性化ペプチド(PACAP)(PAC1);血管作動性腸管ペプチド(VIP/PACAP)(VPAC1、VCAP2);コレシストキニン(CCK);ボンベシン(Pyr-Gln-Arg-Leu-Gly-Asn-Gln-Trp-Ala-Val-Gly-H is-Leu-Met-NH2)/ガストリン放出ペプチド(GRP);ニューロテンシン(NTR1、NTR2、NTR3);サブスタンスP(NK1受容体);ニューロペプチドY(Y1−Y6);RGD(Arg-Gly-Asp)、NGR(Asn-Gly-Arg)、二量体及び多量体環状RGDペプチドを含むホーミングペプチド(cRGDfVを含む。);細胞浸透性ペプチド(CPP);ペプチドホルモン、例えば、テストステロン産生と同様に、卵胞刺激ホルモン(FSH)及び黄体形成ホルモン(LH)を標的化によって作用する、黄体形成ホルモン放出ホルモン(LHRH)アゴニスト及びアンタゴニスト、並びにゴナドトロピン放出ホルモン(GnRH)アゴニストであって、ブセレリン(Pyr-His-Trp-Ser-Tyr-D-Ser(OtBu)-Leu-Arg-Pro-NHEt)、ゴナドレリン(Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2)、ゴセレリン(Pyr-His-Trp-Ser-Tyr-D-Ser(OtBu)-Leu-Arg-Pro-AzGly-NH2)、ヒストレリン(Pyr-His-Trp-Ser-Tyr-D-His(N-benzyl)-Leu-Arg-Pro-NHEt)、ロイプロリド(Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt)、ナファレリン(Pyr-His-Trp-Ser-Tyr-2Nal-Leu-Arg-Pro-Gly-NH2)、トリプトレリン(Pyr-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2)、ナファレリン、デスロレリン、アバレリックス(Ac-D-2Nal-D-4-chloroPhe-D-3-(3-pyridyl)Ala-Ser-(N-Me)Tyr-D-Asn-Leu-isopropylLys-Pro-DAla-NH2)、セトロレリックス(Ac-D-2Nal-D-4-chloroPhe-D-3-(3-pyridyl)Ala-Ser-Tyr-D-Cit-Leu-Arg-Pro-D-Ala-NH2)、デガレリックス(Ac-D-2Nal-D-4-chloroPhe-D-3-(3-pyridyl)Ala-Ser-4-aminoPhe(L-hydroorotyl)-D-4-aminoPhe(carba-moyl)-Leu-isopropylLys-Pro-D-Ala-NH2)、及びガニレリックス(Ac-D-2Nal-D-4-chloroPhe-D-3-(3-pyridyl)Ala-Ser-Tyr-D-(N9, N10-diethyl)-homoArg-Leu-(N9, N10-diethyl)-homoArg-Pro-D-Ala-NH2)を含む;トール様受容体 (TLRs)、C型レクチン、及びNodlike受容体(NLRs)を含むパターン認識受容体(PRRs);ナノボディ(VHH(カメリドIg)の誘導体);ドメイン抗体(dAb、VH又はVLドメインの誘導体);二重特異性T細胞エンゲージャー(BiTE、二重特異性二量体);二重親和性再標的化(DART、二重特異性二量体);四価タンデム抗体(TandAb、二重特異性二量体);アンチカリン(リポカリン類の誘導体);アドネクチン類(第10FN3(フィブロネクチン));設計されたアンキリンリピートタンパク質(DARPins);アビマー(Avimer);EGF受容体及びVEGF受容体。
- 前記「Drug1」及び「Drug2」は、チューブリシン類、カリケアマイシン類、オーリスタチン類、メイタンシノイド類、CC−1065類縁体、ダウノルビシン及びドキソルビシン化合物、タキサノイド類(タキサン類)、クリプトフィシン類、エポチロン類、ベンゾジアゼピン二量体(ピロロベンゾジアゼピン(PBD)、トマイマイシン、アントラマイシン、インドリノベンゾジアゼピン類、イミダゾベンゾチアジアゼピン、又はオキサゾリジノベンゾジアゼピン類の二量体を含む。)、カリケアマイシン類及びエンジイン類抗生物質、アクチノマイシン、アザセリン類、ブレオマイシン類、エピルビシン、タモキシフェン、イダルビシン、ドラスタチン類/オーリスタチン類(モノメチルオーリスタチンE、MMAE、MMAF、オーリスタチンPYE、オーリスタチンTP、オーリスタチン2−AQ、6−AQ、EB(AEB)、及びEFP(AEFP)を含む。)、デュオカルマイシン類、チオテパ、ビンクリスチン類、ヘミアステリン類、ナズマミド類(nazumamides)、ミクロギニン類(microginins)、ラジオスミン類(radiosumins)、アルテロバクチン類(alterobactins)、ミクロスクレロデルミシン類(microsclerodermins)、テネラミド類(thenellamides)、エスペラミシン類(esperamicins)、siRNA、核酸分解酵素、並びに/又は上記分子のいずれかの薬学的に許容される塩、酸、又は/及びそれらの類縁体及び誘導体から選択される、請求項2又は4に記載の化合物。
- 前記細胞結合剤/分子は、抗体、タンパク質、ビタミン(葉酸類を含む。)、ペプチド、ポリマーミセル、リポソーム、リポタンパク系薬物担体、ナノ粒子薬物担体、デンドリマー、及び細胞結合リガンドで被覆された分子、又はそれらの組み合わせから選択される、請求項2又は3に記載の化合物。
- 前記細胞結合分子/剤は、抗体、全長抗体(ポリクローナル抗体、モノクローナル抗体、二量体、多量体、多重特異性抗体(二重特異性抗体を含む));単鎖抗体、標的細胞と結合する抗体断片、モノクローナル抗体、単鎖モノクローナル抗体、標的細胞と結合するモノクローナル抗体断片、キメラ抗体、標的細胞と結合するキメラ抗体断片、ドメイン抗体、標的細胞と結合するドメイン抗体断片、表面再構成型抗体、単鎖表面再構成型抗体、標的細胞と結合する表面再構成型抗体断片、ヒト化抗体、表面再構成型ヒト化抗体、単鎖ヒト化抗体、標的細胞と結合するヒト化抗体断片、抗イディオタイプ(抗Id)抗体、CDR、二量体、三量体、四量体、ミニ抗体、小分子免疫タンパク質(SIP)、リンホカイン、ホルモン、ビタミン、成長因子、コロニー刺激因子、又は栄養輸送分子である、請求項2、3、及び11のいずれか1項に記載の化合物。
- 前記細胞結合分子/剤は、腫瘍細胞、ウイルス感染細胞、微生物感染細胞、寄生虫感染細胞、自己免疫疾患細胞、活性化腫瘍細胞、骨髄細胞、活性化T細胞、影響されているB細胞、又はメラニン細胞を標的とすることができる薬剤である、請求項2、3、及び11のいずれか1項に記載の化合物。
- 前記細胞結合分子/剤は、以下のいずれかの抗原又は受容体に対して可能である、請求項2、3、及び11のいずれか1項に記載の化合物:CD3、CD4、CD5、CD6、CD7、CD8、CD9、CD10、CD11a、CD11b、CD11c、CD12w、CD14、CD15、CD16、CDw17、CD18、CD19、CD20、CD21、CD22、CD23、CD24、CD25、CD26、CD27、CD28、CD29、CD30、CD31、CD32、CD33、CD34、CD35、CD36、CD37、CD38、CD39、CD40、CD41、CD42、CD43、CD44、CD45、CD46、CD47、CD48、CD49b、CD49c、CD51、CD52、CD53、CD54、CD55、CD56、CD58、CD59、CD61、CD62E、CD62L、CD62P、CD63、CD66、CD68、CD69、CD70、CD72、CD74、CD79、CD79a、CD79b、CD80、CD81、CD82、CD83、CD86、CD87、CD88、CD89、CD90、CD91、CD95、CD96、CD98、CD100、CD103、CD105、CD106、CD109、CD117、CD120、CD125、CD126、CD127、CD133、CD134、CD135、CD138、CD141、CD142、CD143、CD144、CD147、CD151、CD147、CD152、CD154、CD156、CD158、CD163、CD166、CD168、CD174、CD180、CD184、CDw186、CD194、CD195、CD200、CD200a、CD200b、CD209、CD221、CD227、CD235a、CD240、CD262、CD271、CD274、CD276(B7−H3)、CD303、CD304、CD309、CD326、 4−1BB、5AC、5T4(栄養芽細胞糖タンパク質、TPBG、5T4、Wnt活性化阻害因子1又はWAIF1)、腺癌抗原、AGS−5、AGS−22M6、アクチビン受容体様キナーゼ1、AFP、AKAP−4、ALK、αインテグリン、αvβ6、アミノペプチダーゼN、アミロイドβ、アンドロゲン受容体、アンジオポイエチン2、アンジオポイエチン3、アネキシンA1、炭疽菌トキシン防御抗原、抗トランスフェリン受容体、AOC3(VAP−1)、B7−H3、炭疽菌、BAFF(B−細胞活性化因子)、B−リンパ腫細胞、bcr−abl、ボンベシン、BORIS、C5、C242抗原、CA125(炭水化物抗原125、MUC16)、CA−IX(又はCAIX、炭酸脱水酵素9)、CALLA、CanAg、イヌIL31、炭酸脱水酵素IX、心筋ミオシン、CCL11(C−Cモチーフケモカイン11)、CCR4(CCケモカイン受容体4型、CD194)、CCR5、CD3E(イプシロン)、CEA(癌胎児性抗原)、CEACAM3、CEACAM5(癌胎児性抗原)、CFD(因子D)、Ch4D5、コレシストキニン2(CCK2R)、CLDN18(クラウディン−18)、クランピング因子A、CRIPTO、FCSF1R(コロニー刺激因子1受容体、CD115)、CSF2(コロニー刺激因子2、顆粒球マクロファージコロニー刺激因子(GM−CSF))、CTLA4(細胞傷害性Tリンパ球関連タンパク質4)、CTAA16.88腫瘍抗原、CXCR4(CD184)、CXCケモカイン受容体4型、cADPリボースヒドロラーゼ、Cyclin B1、CYP1B1、サイトメガロウイルス、サイトメガロウイルス糖タンパク質B、ダビガトラン、DLL4(デルタ様リガンド4)、DPP4(ジペプチジルペプチダーゼ4)、DR5(デスレセプター5)、大腸菌志賀毒素2型、ED−B、EGFL7(タンパク質7含有EGF様ドメイン)、EGFR、EGFRII、EGFRvIII、エンドグリン(CD105)、エンドセリンB受容体、エンドトキシン、EpCAM(上皮細胞接着分子)、EphA2、エピシアリン、ERBB2(上皮成長因子受容体2)、ERBB3、ERG(TMPRSS2ETS融合遺伝子)、大腸菌、ETV6−AML、FAP(線維芽細胞活性化タンパク質α)、FCGR1、α−フェトプロテイン、フィブリンII、β鎖、フィブロネクチン外部ドメインB、FOLR(葉酸受容体)、葉酸受容体α、葉酸ヒドロラーゼ、Fos関連抗原1、RSウイルスのFタンパク質、Frizzled受容体、フコシルGM1、GD2ガングリオシド、G−28(細胞表面糖脂質抗原)、GD3イディオタイプ、GloboH、グリピカン3、N−グリコリルノイラミン酸、GM3、GMCSF受容体α鎖、成長分化因子8、GP100、GPNMB(膜貫通タンパク質NMB)、GUCY2C(グアニル酸シクラーゼ2C、グアニル酸シクラーゼC(GC−C)、腸グアニル酸シクラーゼ、グアニル酸シクラーゼ−C受容体、熱安定性エンテロトキシン受容体(hSTAR))、熱ショックタンパク質、血球凝集素、B型肝炎表面抗原、B型肝炎ウイルス、HER1(ヒト上皮成長因子受容体1)、HER2、HER2/neu、HER3(ERBB−3)、IgG4、HGF/SF(幹細胞増殖因子/細胞分散因子)、HHGFR、HIV−1、ヒストン複合体、HLA−DA(ヒト白血球抗原)、HLA−DR10、HLA−DRB、HMWMAA、ヒト絨毛性ゴナドトロピン、HNGF、ヒト細胞散乱因子受容体キナーゼ、HPV E6/E7、Hsp90、hTERT、ICAM−1(細胞間接着分子1)、イディオタイプ、IGF1R(IGF−1、インスリン様増殖因子1受容体)、IGHE、IFN−γ、インフルエンザ赤血球凝集素、IgE、IgE Fc領域、IGHE、IL−1、IL−2受容体(インターロイキン2受容体)、IL−4、IL−5、IL−6、IL−6R(インターロイキン6受容体)、IL−9、IL−10、L−12、IL−13、IL−17、IL−17A、IL−20、IL−22、IL−23、IL−31RA、ILGF2(インスリン様増殖因子2)、インテグリン(α4、αIIIbβ3、αvβ3、α4β7、α5β1、α6β4、α7β7、αIIβ3、α5β5、αvβ5)、インターフェロンγ誘導タンパク質、ITAGA2、ITGB2、KIR2D、LCK、Le、レグマイン、ルイス−Y抗原、LFA−1(リンパ球機能関連抗原1、CD11a)、LHRH、LINGO−1、リポタイコ酸、LIV1A、LMP2、LTA、MAD−CT−1、MAD−CT−2、MAGE−1、MAGE−2、MAGE−3、MAGEA1、MAGEA3、MAGEA4、MART1、MCP−1、MIF(マクロファージ遊走阻止因子又はグリコシル化阻害因子(GIF))、MS4A1(膜貫通4ドメインサブファミリーAメンバー1)、MSLN(メソテリン)、MUC1(ムチン1、細胞表面関連(MUC1)又はPolymorphic epithelial mucin(PEM))、MUC1−KLH、MUC16(CA125)、MCP1(単球走化性タンパク質1)、MelanA/MART1、ML−IAP、MPG、MS4A1(膜貫通型4ドメインサブファミリーA)、MYCN、ミエリン関連糖タンパク質、ミオスタチン、NA17、NARP−1、NCA−90(顆粒球抗原)、Nectin−4(ASG−22ME)、NGF、神経アポトーシス制御プロテイナーゼ1、NOGO−A、Notch受容体、ヌクレオリン、Neu癌遺伝子産物、NY−BR−1、NY−ESO−1、OX−40、OxLDL(酸化低密度リポタンパク質)、OY−TES1、P21、p53非変異体、P97、Page4、PAP、、抗(N−グリコリルノイラミン酸)のパラトープ、PAX3、PAX5、PCSK9、PDCD1(PD−1、プログラムされた細胞死タンパク質1、CD279)、PDGF−Rα、(血小板由来成長因子受容体α)、PDGFR−β、PDL−1、PLAC1、PLAP様精巣アルカリホスファターゼ、血小板由来成長因子受容体β、リン酸ナトリウム共輸送体、PMEL17、ポリシアル酸、プロテイナーゼ3(PR1)、前立腺癌、PS(ホスファチジルセリン)、前立腺癌細胞、緑膿菌、PSMA、PSA、PSCA、狂犬病ウイルス糖タンパク質、RHD(Rhポリペプチド1(RhPI)、CD240)、アカゲザル因子(Rhesus factor)、RANKL、PhoC,Ras変異体、RG55、ROBO4、RSウイルス、RON、肉腫転移ブレイクポイント、SART3、スクレロスチン、SLAMF7(SLAMファミリーメンバー7)、セレクチンP、SDC1(シンデカン1)、sLe(a)、ソマトメジンC、SIP(スフィンゴシン−1−ホスフェート)、ソマトスタチン、精子タンパク質17、SSX2、STEAP1(前立腺1の6回膜貫通上皮抗原)、STEAP2、STn、TAG−22(腫瘍関連糖タンパク質72)、サバイビン、T細胞受容体、T細胞膜貫通タンパク質、TEM1(腫瘍上皮マーカー1)、TENB2、テナスシンC(TN−C)、TGF−α、TGF−β(トランスフォーミング増殖因子β)、TGF−β1、TGF−β2(トランスフォーミング増殖因子β2)、Tie(CD202b)、Tie2、TIM−1(CDX−014)、TN、TNF、TNF−α、TNFRSF8、TNFRSF10B(腫瘍壊死因子受容体スーパーファミリーメンバー10B)、TNFRSF13B(腫瘍壊死因子受容体スーパーファミリーメンバー13B)、TPBG(栄養膜糖タンパク質)、TRAIL−R1(腫瘍壊死アポトーシス誘導リガンド受容体1)、TRAILR2(細胞死受容体5(DR5))、主要関連カルシウムシグナルトランスデューサー2、MUC1の腫瘍特異的グリコシル化、TWEAK受容体、TYRP1(糖タンパク質75)、TRP−2、チロシナーゼ、VCAM−1(CD106)、VEGF、VEGF−A、VEGF−2(CD309)、VEGFR−1、VEGFR2、又はビメンチン、WT1、XAGE1、又は任意のインスリン成長因子受容体を発現する細胞、又は任意の上皮増殖因子受容体。
- 前記腫瘍細胞は、リンパ腫細胞、骨髄腫細胞、腎細胞、乳癌細胞、前立腺癌細胞、卵巣癌細胞、大腸癌細胞、胃癌細胞、扁平上皮癌細胞、小細胞肺癌細胞、非小細胞肺癌細胞、又は精巣癌細胞から選択される、請求項13に記載の化合物。
- 前記連結体成分R1及び/又はR2は、6−マレイミドカプロイル(MC)、マレイミドプロパノイル(MP)、バリン−シトルリン(val−cit)、アラニン−フェニルアラニン(ala−phe)、リジン−フェニルアラニン(lys−phe)、p−アミノベンジルオキシカルボニル(PAB)、4−チオ−ペンタン酸エステル(SPP)、4−(N−マレイミドメチル)シクロヘキサン−1−カルボン酸エステル(MCC)、4−チオ−酪酸エステル(SPDB)、マレイミドエチル(ME)、4−チオ−2−ヒドロキシスルホニル−酪酸エステル(2−sulfo−SPDB)、ピリジニル−ジチオール(PySS)、アルコキシアミノ(AOA)、エチレンオキシ(EO)、4−メチル−4−ジチオエステル−ペンタン酸(MPDP)、ジチオ、ペプチド、及び/又は(4−アセチル)アミノ安息香酸(SIAB)の連結体成分の一種又は二種以上にて構成されてもよい、請求項1〜4のいずれか1項に記載の化合物。
- 「Drug1」及び「Drug2」がチューブリシン(Tubulysin)類縁体であり、以下のT01、T02、T03、T04、T05、T06、及びT07の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
Z3及びZ’3は独立して、H、OP(O)(OM1)(OM2)、OCH2OP(O)(OM1)(OM2)、OSO3M1、R1、又はO−配糖体(グルコシド, ガラクトシド、マンノシド、グルクロノシド、アロシド、フルクトシド)、NH−配糖体、S−配糖体若しくはCH2−配糖体であり;
M1及びM2は独立してH、Na、K、Ca、Mg、NH4、NR1R2R3であり;
nは1〜30であり;
X1、X2、R1、R2、及びR3は、請求項1及び2で定義されているものと同じである。 - 「Drug1」及び「Drug2」がCC−1065類縁体及び/又はデュオカルマイシン(duocarmycin)類縁体であり、以下のCC01、CC02、及びCC03の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
nは1〜30であり;
Z4及びZ’4は独立して、H、PO(O)(OM1)(OM2)、CH2PO(O)(OM1)(OM2)、SO3M1、CH3N(CH2CH2)2NC(O)−、O(CH2CH2)2NC(O)−、R1、又は配糖体であり;
X3及びX’3は独立して、O、NH、NHC(O)、OC(O)、−C(O)O、若しくはR1であるか、又は存在しない;
X1、X2、R1、R2、M1、及びM2は、請求項1及び2で定義されているものと同じである。 - 「Drug1」及び「Drug2」がオーリスタチン及びドラスタチン(dolastatin)類縁体であり、以下のAu01、Au02、Au03、Au04、及びAu05の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
nは1〜30であり;
X3及びX’3は独立して、CH2、O、NH、NHC(O)、NHC(O)NH、C(O)、若しくはOC(O)R1であるか、又は存在せず;
X4及びX4’は独立して、CH2、C(O)、C(O)NH、C(O)N(R1)、R1、NHR1、NR1、C(O)R1、又はC(O)Oであり;
Z3及びZ’3は独立して、H、R1、OP(O)(OM1)(OM2)、NHR1、OCH2OP(O)(OM1)(OM2)、OSO3M1、又はO−配糖体(グルコシド, ガラクトシド、マンノシド、グルクロノシド、アロシド、フルクトシド)、NH−配糖体、S−配糖体若しくはCH2−配糖体であり;
M1及びM2は独立してH、Na、K、Ca、Mg、NH4、NR1R2R3であり;
X1、X2、R1、R2、及びR3は、請求項1及びで定義されているものと同じである。 - 「Drug1」及び「Drug2」がベンゾジアゼピン二量体類縁体であり、以下のPB01、PB02、PB03、PB04、PB05、PB06、PB07、PB08、PB09、PB10、及びPB11の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
nは1〜30であり;
X3及びX’3は独立して、CH2、O、NH、NHC(O)、NHC(O)NH、C(O)、OC(O)、OC(O)(NR3)、R1、NHR1、NR1、C(O)R1、若しくはC(O)Oであるか、又は存在せず;
X4及びX’4は独立して、CH2、C(O)、C(O)NH、C(O)N(R1)、R1、NHR1、NR1、C(O)R1、又はC(O)Oであり;
M1及びM2は独立してH、Na、K、Ca、Mg、NH4、NR1R2R3であり;
X1、X2、R1、R2、及びR3は、請求項1及び2で定義されているものと同じであり、加えて、R1及び/又はR2は存在しなくてもよい。 - 前記「Drug1」及び「Drug2」が、チューブリシン類、メイタンシノイド類、タキサノイド類(タキサン類)、CC−1065類縁体、ダウノルビシン及びドキソルビシン化合物、ベンゾジアゼピン二量体(ピロロベンゾジアゼピン(PBD)、トマイマイシン、アントラマイシン、インドリノベンゾジアゼピン類、イミダゾベンゾチアジアゼピン、又はオキサゾリジノベンゾジアゼピン類の二量体を含む。)、カリケアマイシン類及びエンジイン類抗生物質、アクチノマイシン、アザセリン類、ブレオマイシン類、エピルビシン、タモキシフェン、イダルビシン、ドラスタチン類、オーリスタチン類(モノメチルオーリスタチンE、MMAE、MMAF、オーリスタチンPYE、オーリスタチンTP、オーリスタチン2−AQ、6−AQ、EB(AEB)、及びEFP(AEFP)を含む。)、デュオカルマイシン類、チオテパ、ビンクリスチン類、ヘミアステリン類、ナズマミド類(nazumamides)、ミクロギニン類(microginins)、ラジオスミン類(radiosumins)、アルテロバクチン類(alterobactins)、ミクロスクレロデルミシン類(microsclerodermins)、テオネラミド類(theonellamides)、エスペラミシン類(esperamicins)、PNU−159682、並びにそれらの類縁体及び誘導体のいずれかの組み合わせから選択される2つの異なる細胞毒性剤であり、以下のZ01、Z02、Z03、Z04、Z05、Z06、Z07、Z08、Z09、Z10、Z11、Z12、Z13、Z14、Z15、Z16、Z17、及びZ18の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
nは1〜30であり;
X3及びX’3は独立して、CH2、O、NH、NHC(O)、NHC(O)NH、C(O)、OC(O)、OC(O)(NR3)、R1、NHR1、NR1、若しくはC(O)R1であるか、又は存在せず;
X4及びX’4は独立して、H、CH2、OH、O、C(O)、C(O)NH、C(O)N(R1)、R1、NHR1、NR1、C(O)R1、又はC(O)Oであり;
M1及びM2は独立してH、Na、K、Ca、Mg、NH4、NR1R2R3であり;
X1、X2、R1、R2、及びR3は、請求項1及び2で定義されているものと同じであり、加えて、R1及び/又はR2は存在しなくてもよい。 - 「Drug1」及び「Drug2」が細胞結合リガンド又は受容体類縁体であり、前記式(II)の共役体化合物が、以下のLB01(PMSAリガンド共役体)、LB02(葉酸受容体共役体)、LB03(ソマトスタチン受容体共役体)、LB04(オクトレオチド、ソマトスタチン類縁体受容体共役体)、LB05(ランレオチド、ソマトスタチン類縁体受容体共役体)、LB06(CAIX受容体共役体)、LB07(CAIX受容体共役体)、LB08(黄体形成ホルモン放出ホルモン(LH−RH)リガンド及びGnRH共役体)、LB09(黄体形成ホルモン放出ホルモン(LH−RH)及びGnRHリガンド共役体)、LB10(GnRHアンタゴニスト、アバレリックス共役体)、LB11(コバラミン、VB12類縁体共役体)、LB12(ガストリン放出ペプチド受容体(GRPr)、MBA共役体)、LB13(αvβ3インテグリン受容体、環状RGDペンタペプチド共役体)、LB14(VEGF受容体共役体のヘテロ二価ペプチドリガンド)、LB15(ニューロメジンB共役体)、LB16(Gタンパク質共役受容体、ボンベシン共役体)、及びLB17(Toll様受容体、TLR2共役体)の構造である、請求項2に記載の化合物:
式中:
mAbは抗体であり;
nは1〜30であり;
X3及びX’3は独立して、CH2、O、NH、NHC(O)、NHC(O)NH、C(O)、OC(O)、OC(O)(NR3)、R1、NHR1、NR1、若しくはC(O)R1であるか、又は存在せず;
X4及びX’4は独立して、H、CH2、OH、O、C(O)、C(O)NH、C(O)N(R1)、R1、NHR1、NR1、C(O)R1、又はC(O)Oであり;
M1及びM2は独立してH、Na、K、Ca、Mg、NH4、NR1R2R3であり;
m3及びm4は独立して0〜5000であり;
X1、X2、R1、R2、及びR3は、請求項1及び2で定義されているものと同じであり、加えて、R1及び/又はR2は存在しなくてもよい。 - 前記連結体成分R1及び/又はR2の内部に、1〜20単位の天然又は非天然のアミノ酸のペプチド、p−アミノベンジル単位、6−マレイミドカプロイル単位、ジスルフィド単位、チオエーテル単位、ヒドラゾン単位、トリアゾール単位、又はアルコキシム単位のいずれかを含む、請求項2、17〜27のいずれか1項に記載の化合物。
- 前記連結体成分R1及び/又はR2がプロテアーゼにより開裂可能である、請求項2、17〜27のいずれか1項に記載の化合物。
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JP2021073185A (ja) * | 2015-08-10 | 2021-05-13 | ハンジョウ ディーエーシー バイオテック シーオー.,エルティディ.Hangzhou Dac Biotech Co.,Ltd. | 新規な連結体及び生体分子と薬物との特異的共役におけるその使用 |
JP7330515B2 (ja) | 2015-08-10 | 2023-08-22 | ハンジョウ ディーエーシー バイオテック シーオー.,エルティディ. | 新規な連結体及び生体分子と薬物との特異的共役におけるその使用 |
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WO2015155753A3 (en) | 2016-06-30 |
CA2991975A1 (en) | 2015-10-15 |
WO2015155753A2 (en) | 2015-10-15 |
CN108289964B (zh) | 2022-08-12 |
CN108289964A (zh) | 2018-07-17 |
CN115300640A (zh) | 2022-11-08 |
CA2991975C (en) | 2021-04-06 |
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