JP6332773B2 - 薬物と細胞結合分子との共役のための新規細胞毒性分子 - Google Patents
薬物と細胞結合分子との共役のための新規細胞毒性分子 Download PDFInfo
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Description
が単結合又は二重結合を表し、
が単結合である場合、U及びU’がそれぞれ独立してH、R5、アミン保護基、細胞結合分子と接続するための反応基を含む連結体(L’)、又は当該位置で接続している細胞結合分子を表す;
「アルキル」とは、鎖中又は環中に1〜8個の炭素原子を有する直鎖状又は分岐してもよい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以上の低級アルキル基、例えばメチル、エチル又はプロピルが結合されていることを意味する。アルキルの具体例としては、メチル、エチル、n−プロピル、イソプロピル、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、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のものでもよく、1以上の基で置換されていてもよい。該基にはC1〜C8アルキル、−O−(C1〜C8)、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’、−S(O)2R’、 −S(O)R’、−OH、−ハロゲン(F、Cl、Br、I)、−N3、−NH2、−NH(R’)、−N(R’)2及び−CNが含まれるが、これらに限定されない。尚、R’とはC1〜C8アルキル又はアリールを表す。
−モノクローナル抗体(mAb);
−一本鎖抗体;
−Fab、Fab’、F(ab’)2及びFv等の抗体フラグメント(Parham, J. Immunol., 1983, 131, 2895-2902; Spring, et al., J. Immunol., 1974, 113, 470-478; Nisonoff, et al., Arch. Biochem. Biophys., 1960, 89, 230-244)、Fab発現ライブラリにより得られる断片、抗イディオ(anti−Id)抗体、CDR’s、及び上記免疫特異的に癌細胞抗原、ウイルス抗原又は微生物抗原と結合する上記の抗原決定基結合断片。
−インターフェロン;
−ペプチド又は共役タンパク質若しくは共役ポリペプチド;
−IL−2、IL−3、IL−4、IL−5及びIL−6等のリンホカイン;
−インスリン、TRH(甲状腺刺激ホルモン放出ホルモン)、MSH(メラノサイト刺激ホルモン)、並びにアンドロゲン及びエストロゲン等のステロイドホルモン等のホルモン類;
−EGF、TGFα、インスリン様成長因子(IGF−I、IGF−II)、G−CSF、M−CSF及びGM−CSF(Burgess, Immunology Today, 1984, 5, 155-158)、並びに葉酸等のビタミン等の成長因子及びコロニー刺激因子;
−トランスフェリン(O'Keefe, et al., J. Biol. Chem., 1985,260, 932-937) 。
本発明のPBD二量体誘導体は、任意に結合基を介して細胞結合分子と結合し、又は結合できる、一つの又は複数のピロール[2,1−c][1,4]ベンゾジアゼピン誘導体を含む。前記結合基は、一般的な方法によりピロール[2,1−c][1,4]ベンゾジアゼピン誘導体と共有的に結合される化学的残基の一部である。
が単結合又は二重結合を表し、
が単結合である場合、U及びU’がそれぞれ独立してH、R5、アミン保護基、細胞結合分子と接続するための反応基を含む連結体(L’)、又は当該位置で接続している細胞結合分子を表す。
本発明の化合物及び方法は、当業者に既知の各種の方法により得ることができる。これらの化合物は、例えば、実施例の項に記載された方法の適用又は当業者よる適切な変更により合成することができる。適切な調整及び変更は、当業者に容易に理解できるほど明確であり、周知であるかあるいは当業者が化学論文から容易に知得することができる。特に、そのような方法は、Richard C. Larock, Comprehensive Organic Transformations, A Guide to Functional Group Preparations, vol II, 2nd Ed., Wiley Publishers, 2010に見出される。
本発明は、架橋連結体(L)の接続基を通じて細胞結合分子と共有的に接続されたPBD誘導体の少なくとも1つを含む共役分子も提供する。前記共役体として好ましくは、1〜20分子の本発明のPBD誘導体と細胞結合分子とが、PBD誘導体の連結体の接続基を通じて共有的に接続されていることを含む。
azumab)(抗大腸菌抗体)、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)。
)安息香酸エステル)が含まれる。
本発明の細胞接着分子−薬物共役体、特に抗体−薬物共役体(ADC)は、腫瘍抗原が過剰に発現することを特徴とするような、様々な疾患及び障害を治療できることが期待される。典型的な状態及び過剰増殖性障害には、良性及び悪性腫瘍、白血病及びリンパ性腫瘍が含まれ、その他に、ニューロン、グリア、アストロサイト、視床下部、腺体、マクロファージ、上皮、基質、胞胚、炎症、血管生成、及び自己免疫疾患を含む免疫系の関連疾患が含まれている。
実験の操作プロセス:非共役遊離薬物又は薬物共役体を96穴平底培養皿に加え、所望のモル範囲をカバーするために段階的に希釈した。抗原陽性(Ag+)又は抗原陰性(Ag−)細胞を特定の細胞密度(1000〜10000細胞/ウェル)となるようにウェルに加え、細胞株及び薬物濃度毎に3つの並列サンプルを調製した。全ての細胞株をRPMI−1640(カタログ番号11875−085、Invitrogen社)で培養し、10%胎児ウシ血清及びゲンタマイシンを補給した。オリフィス板を使い、37℃、5%二酸化炭素の大気下で5日培養した。培養の最後の段階で、WST−8細胞活性検定方法を用い、生細胞をWST−8(2〜7時間)で測定し、細胞毒性を評価した。各ウェルの吸光度を測定し、各濃度での細胞生存率を作図し、共役体の細胞毒効果又は抗原特異性を計算した。抗体−薬物共役体の効力及び特異性は、過量の裸の抗体を加える及び加えない条件の下で、共役体による抗原陽性細胞に対する殺傷効力によって測定した。
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Claims (21)
- 式(I)の化合物又はこれらの薬学的に許容される塩、水和物若しくは水和塩;又はこれらの化合物の多結晶型物質;又はそれらの光学異性体、ラセミ体、ジアステレオマー若しくはエナンチオマー。
式中、
VとV’はそれぞれ独立に、H、−OH、−NHOH;エーテル(−OR5);エステル(−OCOR5、例えばアセテート);カーボネート(−COOR5);アミン(−NR5R5’、−NR5COR5’、−NR5R5’R5’’);カルバメート(−OCONR5R5’);グアニジウム(−NR5(C=NH)NR5’R5’’);アミノ酸又はペプチド(−NR5CO(Aa)t:Aaはアミノ酸又は1〜100個のアミノ酸単位(tはアミノ酸単位の数を表す。)を含むポリペプチドである。);任意に置換された窒素含有5又は6員複素環(ピペリジン、テトラヒドロピロール、ピラゾール、モルホリン等);尿素(−NR5COR5’R5’’);チオカルバメート(−OCSNHR5);チオール(SH);スルフィド;スルホキシド(−SOR5);スルフォン(−SOOR5);亜硫酸(−SO3、HSO3、HSO2、又はHSO3 −、SO3 2−、若しくは−HSO2 −塩);重亜硫酸(−SO3);スルホンアミド(−NR5SOOR5’);メタ重亜硫酸(H2S2O5又はS2O5 2−塩);モノ、ジ、トリ及びテトラチオホスフェート(PO3SH3、PO2S2H2、POS3H2、PS4H2、又はPO3S3−、PO2S2 3−、POS3 3−若しくはPS4 3−の塩);チオホスフェートエステル((R5O)2POSR5’);チオスルフェート(−S2O3H又はS2O3 2−塩);ジチオニト(−S2O4H又はS2O4 2−塩);ホスホロジチオエート(P(=S)(OR5)(S)(OH)又は陽イオンと生成する塩);ヒドロキシルアミン誘導体(−NR5OR5’);ヒドロキサム酸(R5C(=O)NOH又は陽イオンと生成する塩);ホルムアルデヒドスルホキシレート(HOCH2SO2 −又はその塩);アミド(−NR5COR5’);アジド(−N3);シアノ基;ハロゲン;トリアルキル基、アミド亜リン酸エステル(ホスホロアミド酸)、トリアリールホスホニウム、アミノ酸誘導体基;細胞結合分子と接続するための反応基を有する連結体(L’)、又は当該位置で結合している細胞結合分子から選択される。R5、R5’及びR5’’の定義は、後述の通りである;
UとV及び/又はU’とV’が互いに結合し、UとV及び/又はU’とV’が環状化合物の一部分である環状カルバメート、環状チオカルバメート、又は環状アミンを形成してもよい;
l、m、n、l’、m’及びn’は0、1、2、3、4、5又は6の数字であり;
X、X’、Y及びY’はそれぞれ、N、O、S、アルキル、アルケン、又はエーテルであり;
Z及びZ’はそれぞれ、N、CH、C−R5、COH又はCOR5であり、
R1、R2、R3、R4、R1’、R2’、R3’及びR4’は独立してH、任意に置換していてもよい炭素数1〜10の直鎖、分岐若しくは環状アルキル基、アルケニル基、アルキニル基若しくはアリール基、ポリエチレングリコール単位(OCH2CH2)tR5、ハロゲン、グアニジウム[−NR5(C=NH)NR5’R5’’]、−OR5、−NR5R5’、−NO2、−NCO、−NR5COR5’、−SR5、−SOR5で表されるスルホキシド、−SO2R5で表されるスルフォン、スルホネート−SO3 −M+、−SO3H、スルフェート−OSO3 −M+、−OSO3H、−SO2NR5R5’ で表されるスルホンアミド、シアノ基、アジド基、−COR5、−OCOR5、−OCONR5R5’、−CF3、−OR5、アリール基、複素環、P(O)R5R5’ R5’’ 、細胞結合分子と接続するための反応基を有する連結体(L’)、又は当該位置で結合している細胞結合分子から選択される;
R5、R5’及びR5’’はそれぞれ独立して、H、炭素数1〜10の直鎖、分岐鎖又は環状アルキル基、アルケニル基、アルキニル基又はアリール基、ポリエチレングリコール単位−(CH2CH2O)r−R1(rは0〜100であり、R1の定義は前記の通りである。)、任意に置換されていてもよい炭素数6〜18のアリール基、独立してO、N、及びS原子から選択される1以上のヘテロ原子を含み、任意に置換されていてもよい5〜18員環の複素芳香環、独立してN、O、S及びP原子から選択される1〜6個のヘテロ原子を含み、任意に置換されていてもよい3〜18員環の複素環から選択される;R5、R5’及びR5’’は更に、−NR1R2、−COOH、−SO3H、−OR1、−COOR1、−CONR1、−PO2R1R2、−POR1R2R3、−PO3H又は薬用塩から選択される少なくとも1つの置換基により置換されていてもよい;
qは0、1又は2であり;
R2とR3又はR2’とR3’は、互いに結合して=C(二重結合)、=O(ケトン)、=S、=NR5、−C(=O)(R5)−、又は基=CR5R5’を含む二重結合を形成してもよい;
R1とR2、R1’とR2’、R3とR4、又はR3’とR4’は、互いに結合して芳香環、複素環又は複素アリール環を形成してもよい;
L及びL’は、それぞれ独立して連結体、連結体と細胞結合分子(Q)との共有結合により形成されたクラスター、又は細胞接着分子(CBA)と結合できる官能基を含有する連結体である;
L及びL’が連結体である場合、L及びL’が−Ww−(Aa)r−Tt−、−Ww−(Aa)r−Tt−Q、又はQ−Ww−(Aa)r−Ttで表される放出可能連結体であり、式中、Wは拡張ユニットであり、wは0又は1であり、Aaはそれぞれ独立したアミノ酸を含むアミノ酸ユニットであり、rは0〜100の間の整数である。前記拡張ユニットWは、自壊性又は非自壊性ユニット、ペプチドユニット、ヒドラゾン結合、ジスルフィド結合、エステル結合、オキシム結合、アミド結合又はチオエーテル結合を含んでいてもよい;
前記自壊性ユニットは、2−アミノイミダゾール−5−メタノール誘導体、複素環PAB類縁物質、β−グルクロニド、及びo−又はp−アミノベンジルアセタール等の電子構造がパラアミノベンジルカルバモイル(PAB)基と類似する芳香族化合物を含み、好ましくは、前記自壊性ユニットは下記のいずれか1つを含み;
式中、(*)で標識された原子は、追加スペーサー若しくは放出可能連結体単位、細胞毒性分子及び/又は細胞接着分子(CBA)との結合点である;X1、Y1、Z2、及びZ3は独立してNH、O又はSである;Z1は独立してH、NH、O又はSである;vは0又は1である;Q1は独立してH、OH、C1−C6アルキル基、(OCH2CH2)n、F、Cl、Br、I、OR5、SR5、NR5R5’、N=NR5、N=R5、NR5R5’、NO2、SOR5R5’、SO2R5、SO3R5、OSO3R5、PR5R5’、POR5R5’、PO2R5R5’、OPO(OR5)(OR5’)又はOCH2PO(OR5)(OR5’)であり、式中、R5及びR5’の定義が前記の通りである;
非自壊性ユニットは、下記の構造のうちの一つであり;
式中、(*)で標識された原子は、追加スペーサー若しくは放出可能連結体単位、細胞毒性分子及び/又は細胞接着分子(CBA)との結合点である;X1、Y1、Q1、R5及びR5’の定義は前記の通りである;rは0〜100である;m、n及びpは0〜6である;
スペーサー(T)は炭素数1〜10の直鎖、分岐又は環状アルキル、アルケニル、アルキニル、又はアリールであり、また、Tはポリエチレングリコール(−CH2CH2O−)スペーサーでもよい;tは0又は1〜100である。Tは、自身のアミド結合が加水分解された後、環化反応を行うことができる。このようなアミドは、置換された又は置換されていない4−アミノ酪酸アミド、適切に置換されたビシクロ[2.2.1]及びビシクロ[2.2.2]環系、及び2−アミノフェニルプロピオン酸アミドを含む。
更に、L及びL’は、R5、OR5、SR5、NHR5、又はNR5R5’であってもよく、また、式(I)上のR1、R2、R3、R4、R1’、R2’、R3’、R4’、U、U’、V、又はV’もまた、拡張ユニット(Ww)又はスペーサーユニット(Tt)を介してQと連結するのに用いられることができ;
Qは細胞結合分子(CBA)、該細胞結合分子と結合できる官能基、又は細胞結合分子が付着した連結体と反応できる官能基であり、該官能基はチオール、アミン、ヒドラジン、アルコキシアミノ、置換ジスルフィド、マレイミド、ハロアセチル基、カルボキシル基、N−ヒドロキシコハク酸イミドエステル、ケトン、エステル、アルデヒド、アルキニル、アルケニル、又は保護されたチオール若しくはジスルフィド基である。 - 式(I)の化合物が、下記の式(II)、(III)又は(IV)の化合物又はこれらの薬学的に許容される塩、水和物若しくは水和塩;又はこれらの化合物の多結晶型物質;又はそれらの光学異性体、ラセミ体、ジアステレオマー若しくはエナンチオマーである、請求項1記載の化合物。
式中、X、X’、Y、Y’、Z、Z’、l、l’、m、m’、n、n’、R1、R1’、R2、R2’、R3、R3’、R4、R4’、及びLの定義は式(I)と同じである;
V及びV’はそれぞれ独立して、エーテル、エステル、カーボネート、カーバメート、環状カーバメート、尿素、チオカーバメート、環状チオカーバメート、スルフィド、スルホキシド、スルホン、亜硫酸塩、重亜硫酸塩、スルホンアミド、アミン、環状アミン、ヒドロキシルアミン誘導体、アミド、アジド、シアノ、ハロゲン、トリアルキル又はトリアリールホスホニウム、及びアミノ酸誘導基からなる群から選択される;
V’’が(=)O、(=)NH、(=)N−CONR5R5’、(=)N−CONR5、(=)N−COOR5、又は(=)N−O−R5である;
R5、R5’及びR5’’はそれぞれ独立して、H、C1〜C8アルキル、アルケニル、アルキニル、ヘテロアルキル、アリール、アリールアルキル若しくはカルボニルアルキル、又はそれらの薬用塩から選択される。R5、R5’及びR5’’は更に、−N(R1)(R2)、−CO2H、−SO3H、−OR1、−CO2R1、−CONR1、−PO2R1R2、−POR1R2R3、及び−PO3H、又はそれらのNa塩、K塩、Ca塩、アンモニウム塩若しくはその他の薬学的に許容される塩から選択される少なくとも1つの置換基により置換されていてもよい。R5、R5’及びR5’’は、拡張ユニット(Ww)又はスペーサーユニット(Tt)を介して細胞結合分子と結合することもできる。W、w、T及びtの定義は式(I)と同じである; - 式(I)の化合物が、下記の式(V)、(VI)、(VII)、(VIII)、(IX)、(X)、(XI)、(XII)、(XIII)、(XIV)、(XV)、(XVI)若しくは(XII)の化合物又はこれらの薬学的に許容される塩、水和物若しくは水和塩;又はこれらの化合物の多結晶型物質;又はそれらの光学異性体、ラセミ体、ジアステレオマー若しくはエナンチオマーである、請求項1記載の化合物。
は単結合又は二重結合を表す;
U、U’、V、V’、n、n’、X、X’及びLの定義は式(I)と同じである;
R6及びR6’の定義は式(I)中のR5と同じである。R6及びR6’は、拡張ユニット(Ww)又はスペーサーユニット(Tt)を介して細胞結合分子と結合することもできる。W、w、T及びtの定義は式(I)と同じである。 - 連結体Lが、以下の基からなる群から選択される、請求項1記載の化合物;
R5、OR5、SR5、NR5R5’、−(CR5R6)m(Aa)r(CR7R8)n(OCH2CH2)tQ、−(CR5R6)m(CR7R8)n(Aa)r(OCH2CH2)tQ、−(Aa)r(CR5R6)m(CR7R8)n(OCH2CH2)tQ、−(CR5R6)m(CR7R8)n(OCH2CH2)r(Aa)tQ、−(CR5R6)m(CR7=R8)(CR9R10)n(Aa)t(OCH2CH2)rQ、−(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(Aa)t(NR11CO)(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m−フェニル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−フリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−オキサゾリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−チアゾリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−チエニル−(CO)(CR7R8)nQ、−(CR5R6)t−イミダゾリル−(CO)(CR7R8)nQ、−(CR5R6)t−モルホリノ−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−ピペラジノ−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−N−メチルピペラジン−(CO)(Aa)t(CR7R8)nQ、−(CR5R)m−(Aa)tフェニル−Q、−(CR5R6)m−(Aa)tフリル−Q、−(CR5R6)m−オキサゾリル(Aa)t−Q、−(CR5R6)m−チアゾリル(Aa)t−Q、−(CR5R6)m−チエニル(Aa)t−Q、−(CR5R6)m−イミダゾリル(Aa)t−Q、−(CR5R6)m−モルホリノ−(Aa)tQ、−(CR5R6)m−ピペラジノ−(Aa)tQ、−(CR5R6)m−N−ピペラジノ−(Aa)tQ、−K(CR5R6)m(Aa)r(CR7R8)n(OCH2CH2)tQ、−K(CR5R6)m(CR7R8)n(Aa)r(OCH2CH2)tQ、−K(Aa)r(CR5R6)m(CR7R8)n(OCH2CH2)tQ、−K(CR5R6)m(CR7R8)n(OCH2CH2)r(Aa)tQ、−K(CR5R6)m(CR7=R8)(CR9R10)n(Aa)t(OCH2CH2)rQ、−K(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(Aa)t(NR11CO)(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m−フェニル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−フリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−オキサゾリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−チアゾリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−チエニル−(CO)(CR7R8)nQ、−K(CR5R6)t−イミダゾリル−(CO)(CR7R8)nQ、−K(CR5R6)t−モルホリノ−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−ピペラジノ−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−N−メチルピペラジン−(CO)(Aa)t(CR7R8)nQ、−K(CR5R)m−(Aa)tフェニル−Q、−K(CR5R6)m−(Aa)tフリル−Q、−K(CR5R6)m−オキサゾリル(Aa)t−Q、−K(CR5R6)m−チアゾリル(Aa)t−Q、−K(CR5R6)m−チエニル(Aa)t−Q、−K(CR5R6)m−イミダゾリル(Aa)t−Q、−K(CR5R6)m−モルホリノ−(Aa)tQ、−K(CR5R6)m−ピペラジノ−(Aa)tQ、−K(CR5R6)m−N−メチルピペラジノ−(Aa)tQ。
(式中、m、Aa、t、n、Q、R 1 、R 2 、R3、R4及びR5の定義は式(I)におけるのと同じであり;R6、R7 、R8 、R 9 、R 10 、及びR 11 はそれぞれ独立に、H、ハロゲン、C1−C8アルキル基、アリール基、アルケニル基、アルキニル基、エーテル、エステル、アミン又はアミド(これらは1以上のハロゲン、CN、NR1R2、CF3、OR1、アリール基、複素環、S(O)R1、SO2R1、−CO2H、−SO3H、−OR1、−CO2R1、−CONR1、−PO2R1R2、−PO3H又はP(O)R1R2R3で任意に置換されていてもよい。)から選択され;KがNR1、O、S、Se、B又はその他のヘテロ原子である。) - 連結体LがR5、OR5、SR5、又はNR5R5’である場合、U、U’、V、V’、R1、R1’、R2、R2’、R3、R3’、R4、R4’、R6、又はR6’のうちの1つが独立して以下の結合基から選択される、請求項1〜4のいずれか1項に記載の化合物;
−(CR5R6)m(Aa)r(CR7R8)n(OCH2CH2)tQ、−(CR5R6)m(CR7R8)n(Aa)r(OCH2CH2)tQ、−(Aa)r(CR5R6)m(CR7R8)n(OCH2CH2)tQ、−(CR5R6)m(CR7R8)n(OCH2CH2)r(Aa)tQ、−(CR5R6)m(CR7=R8)(CR9R10)n(Aa)t(OCH2CH2)rQ、−(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(Aa)t(NR11CO)(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−(CR5R6)m−フェニル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−フリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−オキサゾリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)m−チアゾリル−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−チエニル−(CO)(CR7R8)nQ、−(CR5R6)t−イミダゾリル−(CO)(CR7R8)nQ、−(CR5R6)t−モルホリノ−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−ピペラジノ−(CO)(Aa)t(CR7R8)nQ、−(CR5R6)t−N−メチルピペラジン−(CO)(Aa)t(CR7R8)nQ、−(CR5R)m−(Aa)tフェニル−Q、−(CR5R6)m−(Aa)tフリル−Q、−(CR5R6)m−オキサゾリル(Aa)t−Q、−(CR5R6)m−チアゾリル(Aa)t−Q、−(CR5R6)m−チエニル(Aa)t−Q、−(CR5R6)m−イミダゾリル−(Aa)t−Q、−(CR5R6)m−モルホリノ−(Aa)tQ、−(CR5R6)m−ピペラジノ−(Aa)tQ、−(CR5R6)m−N−ピペラジノ−(Aa)tQ、−K(CR5R6)m(Aa)r(CR7R8)n(OCH2CH2)tQ、−K(CR5R6)m(CR7R8)n(Aa)r(OCH2CH2)tQ、−K(Aa)r(CR5R6)m(CR7R8)n(OCH2CH2)tQ、−K(CR5R6)m(CR7R8)n(OCH2CH2)r(Aa)tQ、−K(CR5R6)m(CR7=R8)(CR9R10)n(Aa)t(OCH2CH2)rQ、−K(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(Aa)t(NR11CO)(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(NR11CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(OCNR7)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m(CO)(Aa)t(CR9R10)n(OCH2CH2)rQ、−K(CR5R6)m−フェニル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−フリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−オキサゾリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)m−チアゾリル−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−チエニル−(CO)(CR7R8)nQ、−K(CR5R6)t−イミダゾリル−(CO)(CR7R8)nQ、−K(CR5R6)t−モルホリノ−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−ピペラジノ−(CO)(Aa)t(CR7R8)nQ、−K(CR5R6)t−N−メチルピペラジン−(CO)(Aa)t(CR7R8)nQ、−K(CR5R)m−(Aa)tフェニル−Q、−K(CR5R6)m−(Aa)tフリル−Q、−K(CR5R6)m−オキサゾリル(Aa)t−Q、−K(CR5R6)m−チアゾリル(Aa)t−Q、−K(CR5R6)m−チエニル(Aa)t−Q、−K(CR5R6)m−イミダゾリル(Aa)t−Q、−K(CR5R6)m−モルホリノ−(Aa)tQ、−K(CR5R6)m−ピペラジノ−(Aa)tQ、−K(CR5R6)m−N−ピペラジノ−(Aa)tQ。
(式中、m、Aa、t、n、Q、R 1 、R 2 、R3、R4及びR5の定義は式(I)におけるのと同じであり;R6、R7 、R8 、R 9 、R 10 、及びR 11 はそれぞれ独立に、H、ハロゲン、C1−C8アルキル基、アリール基、アルケニル基、アルキニル基、エーテル、エステル、アミン又はアミド(これらは1以上のハロゲン、CN、NR1R2、CF3、OR1、アリール基、複素環、S(O)R1、SO2R1、−CO2H、−SO3H、−OR1、−CO2R1、−CONR1、−PO2R1R2、−PO3H又はP(O)R1R2R3で任意に置換されていてもよい。)から選択され;KがNR1、O、S、Se、B又はその他のヘテロ原子である。) - 細胞結合分子−薬物共役体として、以下の細胞結合分子を含む、請求項1〜8のいずれか1項に記載の化合物:
抗体全長(多クローン又は単クローン抗体);一本鎖抗体;二重特異性抗体、三重特異性抗体、抗体フラグメント(例えば、Fab、Fab’、F(ab’)2、Fv、Fab発現ライブラリで得られるフラグメント、抗イディオタイプ(anti−Id)抗体、CDR’s、及び如何なる癌細胞抗原、ウイルス抗原又は微生物抗原と免疫特異的に結合する上記のいずれかのエピトープ結合フラグメント;インターフェロン;ペプチド;リンホカイン;ホルモン類;成長因子及びコロニー刺激因子;インスリン及びインスリン様成長因子(IGF−I及びIGF−II)、G−CSF、M−CSF並びにGM−CSF;ワクチン成長因子(VGF);線維芽細胞増殖因子(FGFs);小分子量タンパク質、ポリペプチド、ペプチド及びペプチドホルモン;血小板成長因子;インターロイキン及びサイトカイン;ビタミン;アポタンパク質及び糖タンパク質;糖結合タンパク質又はリポタンパク質;細胞栄養素輸送分子(トランスフェリン等);小分子阻害剤;標的細胞と結合する共役されたタンパク質を含むペプチド、ペプチド類縁物質又はタンパク質;非ペプチド又はその他の細胞結合分子又は物質。 - 請求項1、2、3、4、7又は8に記載の化合物及び薬学的に許容される担体を含む、医薬組成物。
- 哺乳動物における異常な細胞成長の抑制又は増殖性疾患の治療のために用いられ、前記疾患が癌、良性又は悪性腫瘍;白血病及びリンパ悪性腫瘍;ニューロン類と神経膠こう細胞類、アストロサイト類、視床下部類、腺体、マクロファージ類、上皮、基質、胞胚、血管生成及び免疫欠損関連疾患;炎症;自己免疫性疾患;構造破壊性疾患;骨組織破壊;伝染性疾患;ウイルス性疾患;繊維化疾患;神経退化性疾患;膵臓又は腎臓疾患を含む、請求項10記載の医薬組成物。
- 任意に相乗効果薬物を含み、該相乗効果薬物が化学療法剤、自己免疫疾患治療剤、抗感染症治療剤、抗ウイルス剤若しくはその他の免疫治療剤、又はこれらの相乗効果薬物のいくつかであり、断続的に又は持続的に哺乳動物に投与できる、請求項11記載の医薬組成物。
- 細胞結合分子−薬物共役体としての化合物であって、抗体、抗体フラグメント、二フラグメント抗体、三フラグメント抗体、表皮成長因子(EGF)、前立腺特異性膜表面抗原 (PSMA) 阻害剤、メラニン細胞刺激(MSH)、甲状腺刺激ホルモン(TSH)、多クローン抗体、成長ホルモンインヒビン、葉酸、蛋白分解酵素阻害剤、雌性ホルモン、雌性ホルモン類縁物質、アンキリン反復タンパク質(DARPins)、又は雄性ホルモン若しくはその類縁物質である細胞結合分子(CBA)を含む、請求項1又は8に記載の化合物。
- 連結体(2)並びに式(3)及び(3’)の単量体分子を、中間生成物(4)を経て結合させ、次いでNaBH4で還元することにより式(I)の化合物を得る工程を含む、請求項1〜8のいずれか1項に記載の化合物又はこれらの薬学的に許容される塩、光学異性体、ラセミ体、ジアステレオマー若しくはエナンチオマーの製造方法であって、
前記連結体(2)は、式(1)のジオールから得ることができ、
式中、
が単結合又は二重結合を表し;
U、U’、V、V’、X、X’、Y、Y’、Z、Z’、l、l’、m、m’、n、n’、R1、R1’、R2、R2’、R3、R3’、R4、R4’及びLの定義は式(I)と同じであり;
LGは、F、Cl、Br、I、トリフラート、メシレート、トシレート、ニトロフェノキシ、ジニトロフェノキシ、ペンタフルオロフェノキシ、又は光延反応を経て活性化された中間基から選択される脱離基であり;
式(I)の化合物が式(7)又は(8)に示すような対称的な分子である場合、該化合物は、式(7)の化合物を得るために連結体化合物(6)と式(3)の単量体分子との直接的な結合を行い、次いで式(8)の化合物を得るためにNaBH4で還元することにより得ることができ、前記連結体化合物(6)は、式(5)のジオールから得ることができ;
式中、
---が選択可能な単結合を表し;
が単結合又は二重結合を表し;
X、X’、Y、Y’、Z、Z’、l、l’、m、m’、n、n’、R1、R1’、R2、R2’、R3、R3’、R4、R4’及びLの定義は式(I)と同じであり;
LGは、F、Cl、Br、I、トリフラート、メシレート、トシレート、ニトロフェノキシ、ジニトロフェノキシ、ペンタフルオロフェノキシ、又は光延反応を経て活性化された中間基から選択される脱離基である、方法。 - 表面再構成された抗体、表面再構成された一本鎖抗体、又は表面再構成された抗体フラグメントである細胞結合分子(CBA)を含む、細胞結合分子−薬物共役体としての請求項1、2、3、4、7又は8に記載の化合物。
- 前記細胞接着分子が好ましくは、ヒト化抗体、ヒト化一本鎖抗体、ヒト化抗体フラグメント、キメラ型抗体、キメラ型抗体フラグメント、ドメイン抗体、又はドメイン抗体フラグメントを含む、請求項1、2、3、4、7又は8に記載の化合物。
- 標的細胞と結合する細胞結合分子を含み、該標的細胞は、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;自己免疫細胞;活性化細胞;骨髄細胞;活性化T細胞若しくはB細胞、又はメラニン細胞;CD4、CD6、CD19、CD20、CD22、CD30、CD33、CD37、CD38、CD40、CD44、CD51、CD56、CD66、CD70、CD74、CD79b、CD80、CD98、CD105、CD106、CD125、CD221、CD227、CD262、CD309、CD326、CEACAM3、CEACAM5、DLL4、cMet、EpCAM、CanAg、CALLA、EGFR、CTLA4、CXCR4、エンドグリン、ERBB2、FCGR1,FOLR、GD2、G−28、GD3イディオタイプ、熱ショックタンパク質、HER1、HLA−DR10、HLA−DRB、IGF1R、IL−2受容体、IL−6R、インテグリン(αvβ3、α5β1、α6β4、α11β3、α5β5、αvβ5)、MAGE−1、MAGE−2、MAGE−3、MAGE4、抗トランスフェリン受容体、p97、MS4A1、MUC1又はMUC1−KLH、MUC16、CA125、CEA,gp100、MART1、MPG、ヌクレオリン、神経癌遺伝子生成物、P21、抗N−ヒドロキシアセチルノイラミン酸パラトープ、PLAP様睾丸アルカリホスファターゼ、PSMA、PSA、ROBO4、TAG72、T細胞膜貫通タンパク質、Tie(CD202b)、TNFRSF10B、TNFRSF13B、TPBG、TRAIL−R1、VCAM−1、VEGF、VEGF−A、VEGF−2(CD309)、Her−2抗原、Her−3抗原が発現している細胞;又はインスリン成長因子受容体、上皮成長因子受容体、若しくは葉酸受容体が発現している細胞から選択される、請求項1、2、3、4、7又は8に記載の細胞結合分子−薬物共役体としての化合物。
- 細胞接着分子上に、反応性のジスルフィド、マレイミド、ハロゲン化アセチル、ヒドラジド、ニトリル、アルキニル、アルキルオキシアミノ、又はアルデヒド基を導入する(共有結合されたCBA−L’’分子を形成する)ために、任意に0〜30%の有機共溶媒を含むpH3〜9の水系緩衝液において、細胞接着分子(CBA)を連結体(L’’)で修飾することと、
次いで、細胞接着分子−薬物分子共役体を生成するために、任意に0〜30%の有機共溶媒を含むpH3〜9の水系緩衝液において、CBA−L’’分子と式(I)中の薬物残基(Drug)とを反応させることと、
を含む、細胞結合分子−薬物共役体としての請求項8記載の化合物の製造方法。 - 薬物残基上に、反応性のジスルフィド、マレイミド、ハロゲン化アセチル基、ヒドラジド、ニトリル、アルキニル、アルキルオキシアミノ、アルデヒド、N−ヒドロキシサクシニルイミド(NHS)エステル、又はペンタフルオロフェニルエステル基を導入する(共有結合されたDrug−L’’分子を形成する)ために、有機溶媒又は任意に0〜99%の有機共溶媒を含むpH3〜9の水系緩衝液において、薬物残基(Drug)を連結体(L’’)で修飾することと、
次いで、細胞接着分子−薬物分子共役体を生成するために、任意に0〜30%の有機共溶媒を含むpH3〜9の水系緩衝液において、Drug−L’’分子と細胞接着分子(CBA)又は事前修飾されたCBAとを反応させることと、
を含む、細胞結合分子−薬物共役体としての請求項8記載の化合物の製造方法。 - 任意に有機共溶媒を0〜30%含むpH3〜9の水系緩衝液中で、細胞接着分子と、ジスルフィド、マレイミド、ハロゲン化アセチル、ヒドラジド、ニトリル、アルキニル、アルキルオキシアミノ、アルデヒド基、N−ヒドロキシサクシニルイミド(NHS)エステル、又はペンタフルオロフェニルエステル等の反応性官能基を有する式(I)の薬物残基と、を直接反応させる工程を含む、請求項8記載の細胞結合分子−薬物共役体の製造方法。
- 癌、自己免疫疾患、伝染性疾患又はウイルス性疾患の治療のために、生体外、体内又は体外を通じて哺乳動物へ有効投与量で投与することに使用できる、請求項1、2、3、4、7又は8に記載の化合物。
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