JP6151707B2 - 薬物内包微小球の形成が可能なn−末端で官能基化されたアミノ酸誘導体 - Google Patents
薬物内包微小球の形成が可能なn−末端で官能基化されたアミノ酸誘導体 Download PDFInfo
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Description
本出願は、本明細書において参照により援用される、2011年10月27日に出願された米国仮特許出願第61/552,423号明細書に対する米国特許法119条(e)に基づく優先権を主張する。
本発明は、国立衛生研究所により付与された認可番号R37 EB000244の下に政府による援助を受けてなされたものである。政府は、本発明に一定の権利を有している。
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーである。)
R6およびR7は、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、および、窒素保護基からなる群から選択されるが;
ただし、R6およびR7の少なくとも1つは、式:
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーである。
化学的定義
特定の官能基および化学的用語の定義を以下により詳細に記載する。化学的要素は、Periodic Table of the Elements,CAS version,Handbook of Chemistry and Physics,75th Ed.の内表紙に従って特定されており、特定の官能基は全体として、ここに記載されているとおりに定義されている。また、有機化学、ならびに、特定の官能性部分および反応性の一般原則は、Organic Chemistry,Thomas Sorrell,University Science Books,Sausalito,1999;Smith and March March’s Advanced Organic Chemistry,5th Edition,John Wiley & Sons,Inc.,New York,2001;Larock,Comprehensive Organic Transformations,VCH Publishers,Inc.,New York,1989;and Carruthers,Some Modern Methods of Organic Synthesis,3rd Edition,Cambridge University Press,Cambridge,1987に記載されている。
または、炭素原子上の2個のジェミナル水素が、基=O、=S、=NN(Rbb)2、=NNRbbC(=O)Raa、=NNRbbC(=O)ORaa、=NNRbbS(=O)2Raa、=NRbbもしくは=NORccで置換されており;
Raaは各場合について独立して、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、3員〜14員ヘテロシクリル、C6〜14アリールおよび5員〜14員ヘテロアリールから選択されるか、または、2つのRaa基が結合されて3員〜14員ヘテロシクリルもしくは5員〜14員ヘテロアリール環を形成しており、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRdd基で置換されており;
Rbbは各場合について独立して、水素、−OH、−ORaa、−N(Rcc)2、−CN、−C(=O)Raa、−C(=O)N(Rcc)2、−CO2Raa、−SO2Raa、−C(=NRcc)ORaa、−C(=NRcc)N(Rcc)2、−SO2N(Rcc)2、−SO2Rcc、−SO2ORcc、−SORaa、−C(=S)N(Rcc)2、−C(=O)SRcc、−C(=S)SRcc、−P(=O)2Raa、−P(=O)(Raa)2、−P(=O)2N(Rcc)2、−P(=O)(NRcc)2、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、3員〜14員ヘテロシクリル、C6〜14アリールおよび5員〜14員ヘテロアリールから選択されるか、または、2個のRbb基が結合されて3員〜14員ヘテロシクリルもしくは5員〜14員ヘテロアリール環を形成しており、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRdd基で置換されており;
Rccは各場合について独立して、水素、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、3員〜14員ヘテロシクリル、C6〜14アリールおよび5員〜14員ヘテロアリールから選択されるか、または、2個のRcc基が結合されて3員〜14員ヘテロシクリルもしくは5員〜14員ヘテロアリール環を形成しており、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRdd基で置換されており;
Rddは各場合について独立して、ハロゲン、−CN、−NO2、−N3、−SO2H、−SO3H、−OH、−ORee、−ON(Rff)2、−N(Rff)2、−N(Rff)3 +X−、−N(ORee)Rff、−SH、−SRee、−SSRee、−C(=O)Ree、−CO2H、−CO2Ree、−OC(=O)Ree、−OCO2Ree、−C(=O)N(Rff)2、−OC(=O)N(Rff)2、−NRffC(=O)Ree、−NRffCO2Ree、−NRffC(=O)N(Rff)2、−C(=NRff)ORee、−OC(=NRff)Ree、−OC(=NRff)ORee、−C(=NRff)N(Rff)2、−OC(=NRff)N(Rff)2、−NRffC(=NRff)N(Rff)2、−NRffSO2Ree、−SO2N(Rff)2、−SO2Ree、−SO2ORee、−OSO2Ree、−S(=O)Ree、−Si(Ree)3、−OSi(Ree)3、−C(=S)N(Rff)2、−C(=O)SRee、−C(=S)SRee、−SC(=S)SRee、−P(=O)2Ree、−P(=O)(Ree)2、−OP(=O)(Ree)2、−OP(=O)(ORee)2、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、3員〜10員ヘテロシクリル、C6〜10アリール、5員〜10員ヘテロアリールから選択され、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRgg基で置換されるか、または、2つのジェミナルRdd置換基が結合してOもしくは=Sを形成していることが可能であり;
Reeは各場合について、独立して、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、C6〜10アリール、3員〜10員ヘテロシクリルおよび3員〜10員ヘテロアリールから選択され、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRgg基で置換されており;
Rffは各場合について、独立して、水素、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、3員〜10員ヘテロシクリル、C6〜10アリールおよび5員〜10員ヘテロアリールから選択されるか、または、2個のRff基が結合されて3員〜14員ヘテロシクリルもしくは5員〜14員ヘテロアリール環を形成しており、ここで、各アルキル、アルケニル、アルキニル、カルボシクリル、ヘテロシクリル、アリールおよびヘテロアリールは、独立して、0、1、2、3、4もしくは5個のRgg基で置換されており;ならびに
Rggは各場合について、独立して、ハロゲン、−CN、−NO2、−N3、−SO2H、−SO3H、−OH、−OC1〜50アルキル、−ON(C1〜50アルキル)2、−N(C1〜50アルキル)2、−N(C1〜50アルキル)3 +X−、−NH(C1〜50アルキル)2 +X−、−NH2(C1〜50アルキル)+X−、−NH3 +X−、−N(OC1〜50アルキル)(C1〜50アルキル)、−N(OH)(C1〜50アルキル)、−NH(OH)、−SH、−SC1〜50アルキル、−SS(C1〜50アルキル)、−C(=O)(C1〜50アルキル)、−CO2H、−CO2(C1〜50アルキル)、−OC(=O)(C1〜50アルキル)、−OCO2(C1〜50アルキル)、−C(=O)NH2、−C(=O)N(C1〜50アルキル)2、−OC(=O)NH(C1〜50アルキル)、−NHC(=O)(C1〜50アルキル)、−N(C1〜50アルキル)C(=O)(C1〜50アルキル)、−NHCO2(C1〜50アルキル)、−NHC(=O)N(C1〜50アルキル)2、−NHC(=O)NH(C1〜50アルキル)、−NHC(=O)NH2、−C(=NH)O(C1〜50アルキル)、−OC(=NH)(C1〜50アルキル)、−OC(=NH)OC1〜50アルキル、−C(=NH)N(C1〜50アルキル)2、−C(=NH)NH(C1〜50アルキル)、−C(=NH)NH2、−OC(=NH)N(C1〜50アルキル)2、−OC(NH)NH(C1〜50アルキル)、−OC(NH)NH2、−NHC(NH)N(C1〜50アルキル)2、−NHC(=NH)NH2、−NHSO2(C1〜50アルキル)、−SO2N(C1〜50アルキル)2、−SO2NH(C1〜50アルキル)、−SO2NH2、−SO2C1〜50アルキル、−SO2OC1〜50アルキル、−OSO2C1〜6アルキル、−SOC1〜6アルキル、−Si(C1〜50アルキル)3、−OSi(C1〜6アルキル)3−C(=S)N(C1〜50アルキル)2、C(=S)NH(C1〜50アルキル)、C(=S)NH2、−C(=O)S(C1〜6アルキル)、−C(=S)SC1〜6アルキル、−SC(=S)SC1〜6アルキル、−P(=O)2(C1〜50アルキル)、−P(=O)(C1〜50アルキル)2、−OP(=O)(C1〜50アルキル)2、−OP(=O)(OC1〜50アルキル)2、C1〜50アルキル、C2〜50アルケニル、C2〜50アルキニル、C3〜10カルボシクリル、C6〜10アリール、3員〜10員ヘテロシクリル、5員〜10員ヘテロアリールであるか;または、2つのジェミナルRgg置換基が結合してOもしくは=Sを形成していることが可能であり;
ここで、X−は対イオンである。
本明細書において用いる、「少なくとも1つの場合」という句の使用は、1つの場合を指すが、例えば、例えば、1、2、3、4、5、6、7、8、9または10の場合、および、100以下の場合といった2つ以上の場合をも包含する。
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたC1〜50ヘテロアルキル、任意により置換されたC2〜50ヘテロアルケニル、任意により置換されたC2〜50ヘテロアルキニル、または、ポリマーである。)
で表されるものを含む。
式(I)の化合物はアミノ酸、直鎖ペプチドおよび直鎖ポリペプチドを含み、これは、式(i)、(ii)もしくは(iii)の基の例えば末端アミノ基、アミノ置換基、および/または、イミノ窒素への1つ以上の共役部位を含む。
式中:
nは0であるか、または、1〜100,000の整数(両端を含む)であり;
mは各場合について、独立して、1、2または3であり;
Zは各場合について、独立して、O、SまたはNRZであり、式中、RZは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)もしくは(iii)の基であり;
R1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、ハロゲン、−ORA1、−N(RA1)2または−SRA1であり;式中、RA1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、窒素原子に結合している場合窒素保護基であるか、または、2つのRA1基が結合して任意により置換された複素環もしくは任意により置換されたヘテロアリール環を形成しており;
R2は、式(i)、(ii)もしくは(iii)の基であり;
R3は、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)もしくは(iii)の基であり;
または、R3およびR1基は結合して任意により置換された5員〜6員複素環を形成しており;
R4は、−ORA4、−N(RA4)2または−SRA4であり;式中、RA4は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、窒素原子に結合している場合窒素保護基であるか、または、2つのRA4基が結合して任意により置換された複素環もしくは任意により置換されたヘテロアリール環を形成しており;
R5は、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;ならびに
式(i)、(ii)および(iii)は:
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーである。
Lは、任意により置換されたアルキレン、任意により置換されたアルケニレン、任意により置換されたアルキニレン、任意により置換されたヘテロアルキレン、任意により置換されたヘテロアルケニレン、任意により置換されたヘテロアルキニレン、任意により置換されたカルボシクリレン、任意により置換されたヘテロシクリレン、任意により置換されたアリーレン、または、任意により置換されたヘテロアリーレン、または、これらの組み合わせであり、ならびに
R6およびR7は、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、および、窒素保護基からなる群から選択されるが;
ただし、R6およびR7の少なくとも1つは式(i)、(ii)もしくは(iii)の基で:
式(II)の化合物は、アミノ酸、ペプチドまたはポリペプチドの第1級または第2級アミンまたはアミドと、式(i−x)のエポキシド、チイランまたはアジリジンとの付加生成物の内部環化を介して調製され得る(スキーム2)。
式中:
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
R1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、ハロゲン、−ORA1、−N(RA1)2または−SRA1であり;式中、RA1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、窒素原子に結合している場合窒素保護基であるか、または、2つのRA1基が結合して任意により置換された複素環もしくは任意により置換されたヘテロアリール環を形成しており;
R8は、水素、式(i)、(ii)もしくは(iii)の基、または、式(v)の基:
式中、Z、R2、R3、R5、mおよびnは式(I)について定義されているとおりであり;
または、R8およびR1基は結合して任意により置換された5員〜6員複素環を形成しており;
Wは各場合について、独立して、O、SまたはNRWであり、式中、RWは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)もしくは(iii)の基であり;および
Yは各場合について、独立して、O、SまたはNRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
式(i)、(ii)および(iii)は:
式中:
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーである。
式中:
Lは、任意により置換されたアルキレン、任意により置換されたアルケニレン、任意により置換されたアルキニレン、任意により置換されたヘテロアルキレン、任意により置換されたヘテロアルケニレン、任意により置換されたヘテロアルキニレン、任意により置換されたカルボシクリレン、任意により置換されたヘテロシクリレン、任意により置換されたアリーレン、または、任意により置換されたヘテロアリーレン、または、これらの組み合わせであり、ならびに
R6およびR7は、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、および、窒素保護基からなる群から選択されるが;
ただし、R6およびR7の少なくとも1つは、式(i)、(ii)もしくは(iii)の基であり:
式(III)の化合物は、同一もしくは異なる2、3、4、5、6、7、8、9または10のアミノ酸の環式縮合物であって、例えば、式(i)の基、(iii)または(iii)の内部アミド窒素、アミノ置換基および/またはイミノ窒素に対する1つ以上の共役部位をさらに含む。このような基は、環化前に(すなわち環化生成物のアミノ酸前駆体に)共役され得るか、または、環化後に共役され得る。
式中:
pは、1〜9の整数(端点を含む)であり;
Qは各場合について、独立して、O、SもしくはNRQであり、ここで、RQは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基または式(i)、(ii)、(iii)の基であり;
R1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、ハロゲン、−ORA1、−N(RA1)2または−SRA1であり;式中、RA1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、窒素原子に結合している場合窒素保護基であるか、または、2つのRA1基が結合して任意により置換された複素環もしくは任意により置換されたヘテロアリール環を形成しており;および
R2は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)もしくは(iii)の基であり;ならびに
式(i)、(ii)および(iii)は:
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーであるが;
ただし、RQ、R2、R6またはR7の少なくとも1つは式(i)、(ii)もしくは(iii)の基である。
式中:
Lは、任意により置換されたアルキレン、任意により置換されたアルケニレン、任意により置換されたアルキニレン、任意により置換されたヘテロアルキレン、任意により置換されたヘテロアルケニレン、任意により置換されたヘテロアルキニレン、任意により置換されたカルボシクリレン、任意により置換されたヘテロシクリレン、任意により置換されたアリーレン、または、任意により置換されたヘテロアリーレン、または、これらの組み合わせであり、ならびに
R6およびR7は、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、および、窒素保護基からなる群から選択されるが;
ただし、R6およびR7の少なくとも1つは、式(i)、(ii)もしくは(iii)の基:
式中、R’、X、Y、RLおよびRPは本明細書において定義されているとおりである。
アミノ酸出発材料から構築されていないが、式(IV)、(V)および(VI)の化合物は、同一の分子式および環式モチーフを共有しており、それ故、式(III−a)の化合物の構造異性体である。本発明は、本発明の例示的なAPPL構造異性体として各々を包含する。
式中:
Qは各場合について、独立して、O、SもしくはNRQであり、式中、RQは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)、(iii)の基であり;
R1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、ハロゲン、−ORA1、−N(RA1)2または−SRA1であり;式中、RA1は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、窒素原子に結合している場合窒素保護基であるか、または、2つのRA1基が結合して任意により置換された複素環もしくは任意により置換されたヘテロアリール環を形成しており;
R2は各場合について、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、窒素保護基、または、式(i)、(ii)もしくは(iii)の基であり;ならびに
式(i)、(ii)および(iii)は:
式中:
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーであるが;
ただし、RQ、R2、R6またはR7の少なくとも1つは、式(i)、(ii)もしくは(iii)の基である。
式中:
Lは、任意により置換されたアルキレン、任意により置換されたアルケニレン、任意により置換されたアルキニレン、任意により置換されたヘテロアルキレン、任意により置換されたヘテロアルケニレン、任意により置換されたヘテロアルキニレン、任意により置換されたカルボシクリレン、任意により置換されたヘテロシクリレン、任意により置換されたアリーレン、または、任意により置換されたヘテロアリーレン、または、これらの組み合わせであり、ならびに
R6およびR7は、独立して、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、および、窒素保護基からなる群から選択されるが;
ただし、R6およびR7の少なくとも1つは、式(i)、(ii)もしくは(iii)の基:
上記の考察から理解されるとおり、APPL、特に式(I)、(III)、(IV)、(V)および(VI)のAPPL化合物の各々は、式(i)、(ii)もしくは(iii):
R’は各場合について、独立して、水素または任意により置換されたアルキルであり;
Xは、O、S、NRXであり、式中、RXは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
Yは、O、S、NRYであり、式中、RYは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、または、窒素保護基であり;
RPは、水素、任意により置換されたアルキル、任意により置換されたアルケニル、任意により置換されたアルキニル、任意により置換されたカルボシクリル、任意により置換されたヘテロシクリル、任意により置換されたアリール、任意により置換されたヘテロアリール、酸素原子に結合している場合酸素保護基、硫黄原子に結合している場合硫黄保護基、または、窒素原子に結合している場合窒素保護基であり;および
RLは、任意により置換されたC1〜50アルキル、任意により置換されたC2〜50アルケニル、任意により置換されたC2〜50アルキニル、任意により置換されたヘテロC1〜50アルキル、任意により置換されたヘテロC2〜50アルケニル、任意により置換されたヘテロC2〜50アルキニル、または、ポリマーである。
本明細書に記載されているとおり、本発明の化合物を提供するために、例えば式(i−x)のエポキシド、チイランもしくはアジリジン、式(ii−x)のα,β−不飽和エステル、チオエステルもしくはアミド、または、式(iii−x)のアルデヒドから選択される1種以上の共役剤がAPPL前駆体で処理されてAPPLがもたらされる。
一定の本発明の化合物が本明細書において特定的に想定されている。例えば、8、9、10、11、12、13および14個の炭素原子を含有する無置換n−アルキルRL基を含む化合物が特定的に想定されている。特定の実施形態において、このような化合物のR1は実施例の表1に定義されているとおりアミノ酸側鎖である。
本発明は、組成物の成分としてのAPPLを想定する。例えば、特定の実施形態においては、APPLもしくはその塩、および、賦形剤を含む組成物が提供されており、ここで、APPLは、アミノ酸、直鎖もしくは環式ペプチドまたは直鎖もしくは環式ポリペプチド、または、これらの構造異性体であり、また、ここで、APPLのアミノもしくはアミド基は式(i)、(ii)もしくは(iii)の基に共役している。特定の実施形態において、式(i)、(ii)もしくは(iii)の基は、APPL骨格に存在するアミノ基に結合している。
本明細書に記載の系によって送達されるべき薬剤は、治療的、診断上または予防剤であり得る」。対象に投与されるべきいずれかの化学化合物は、本明細書に記載の複合体、ピコ粒子、ナノ粒子、ミクロ粒子、ミセルまたはリポソームを用いて送達され得る。薬剤は、有機分子(例えば、治療薬、薬物)、無機分子、核酸、タンパク質、アミノ酸、ペプチド、ポリペプチド、ポリヌクレオチド、標的指向化剤、同位体標識化有機または無機分子、ワクチン、免疫学的薬剤等であり得る。
度々、特定の細胞、細胞の採集または組織を標的とすることが望ましいため、APPL、および、これから調製される複合体、リポソーム、ミセル、ミクロ粒子、ピコ粒子およびナノ粒子は、標的指向化剤または標的指向化領域を含むよう修飾され得る。例えば、APPL骨格は標的指向化領域を含み得る。特定の細胞を標的とする多様な薬剤または領域が技術分野において公知である。例えば、Cotten et al.,Methods Enzym.217:618,1993を参照のこと。標的指向化剤は、粒子全体に含まれていても、または、表面上のみに存在していてもよい。標的指向化剤は、タンパク質、ペプチド、炭水化物、糖タンパク質、脂質、小分子、核酸等であり得る。標的指向化剤は、特定の細胞もしくは組織を標的とするために用いられ得、または、粒子のエンドサイトーシスもしくは食作用を促進するために用いられ得る。標的指向化剤の例としては、これらに限定されないが、抗体、抗体のフラグメント、低密度リポタンパク質(LDL)、トランスフェリン、アシアロ糖タンパク質、ヒト免疫不全ウイルス(HIVウイルス)のgp120エンベロープタンパク質、炭水化素、受容体リガンド、シアル酸、アプタマー等が挙げられる。標的指向化剤が粒子全体に含まれている場合、標的指向化剤は粒子の形成に用いられる混合物に含まれ得る。標的指向化剤が表面上のみに存在する場合、標的指向化剤は、標準的な化学技術を用いて、形成された粒子に会合(すなわち、共有結合、疎水性、水素結合、ファンデルワールスまたは他の相互作用によって)され得る。
本発明においては、APPLがポリヌクレオチドの投与において特に有用であると考えられている。例えば、APPLは第2級または第3級アミンを含み、これらのアミンは束縛されているが、これらは、ポリヌクレオチド(例えば、DNA、RNA、DNAおよび/またはRNAの合成類似体、DNA/RNA水酸化物等)との非共有結合的な相互作用には利用可能である。ポリヌクレオチドまたはその誘導体は、ポリヌクレオチド/APPL非共有結合複合体の形成に好適な条件下でAPPLと接触させられる。APPLとポリヌクレオチドとの相互作用は、ポリヌクレオチドの分解を少なくとも部分的に防止すると考えられている。ポリヌクレオチドの主鎖の電荷が中性化されることによる、中性またはわずかに正電荷の複合体もまた、より容易に細胞の疎水性膜(例えば、細胞質、リソソーム、エンドソーム、核)を通過可能である。特定の実施形態において、複合体はわずかに正に荷電されている。特定の実施形態において、複合体は正のζ−電位を有する。特定の実施形態において、ζ−電位は0〜+30である。
本発明においてはまた、APPLが送達系として有用であると考えられている。APPLは:1)APPLの易動性薬剤を複合化および「保護」する能力;2)エンドソームにおけるpHを緩衝する能力;3)「プロトンスポンジ」として作用し、エンドソーム破壊を生じさせる能力;ならびに、4)負電荷薬剤における電荷を中性化する能力を含む数々の特性を有しており、送達のために特に好適である。
本発明は、ミセルまたはリポソームの調製におけるAPPLの使用をさらに想定している。任意の薬剤がミセルまたはリポソームにさらに含まれていても良い。ミセルおよびリポソームは、疎水性小分子などの疎水性薬剤の送達に特に有用である。ミセルまたはリポソームがポリヌクレオチドと複合化(例えば、内包または覆う)される場合、これは、「リポプレックス」とも称される。ミセルおよびリポソームを調製するための多くの技術が技術分野において公知であり、このような方法のいずれもミセルおよびリポソームを形成するためにAPPLと共に用いられ得る。
10,000を超えるヒト疾患が遺伝子または染色体における異常である遺伝性疾患により引き起こされると推定されている。例えば、McClellan,J.and M.C.King,Genetic heterogeneity in human disease.Cell.141(2):p.210−7;Leachman,S.A.,et al.,Therapeutic siRNAs for dominant genetic skin disorders including pachyonychia congenita.J Dermatol Sci,2008.51(3):p.151−7を参照のこと。癌、重篤な高コレステロール血症および家族性アミロイド神経障害などのこれらの疾病の多くは致死性である。例えば、Frank−Kamenetsky,M.,et al.,Therapeutic RNAi targeting PCSK9 acutely lowers plasma cholesterol in rodents and LDL cholesterol in nonhuman primates.Proc Natl Acad Sci U S A,2008.105(33):p.11915−20;Coelho,T.,Familial amyloid polyneuropathy:new developments in genetics and treatment.Curr Opin Neurol,1996.9(5):p.355−9を参照のこと。FireおよびMello(Fire,A.,et al.,Potent and specific genetic interference by double−stranded RNA in Caenorhabditis elegans.Nature,1998.391(6669):p.806−11)によるRNA干渉(RNAi)を介した遺伝子発現サイレンシングの発見以来、ヒトにおけるRNAiのための治療用途の開発に向けて広範な試みがなされている。例えば、Davis,M.E.,The first targeted delivery of siRNA in humans via a self−assembling,cyclodextrin polymer−based nanoparticle:from concept to clinic.Mol Pharm,2009.6(3):p.659−68;Whitehead,K.A.,R.Langer,and D.G.Anderson,Knocking down barriers:advances in siRNA delivery.Nat.Rev.Drug Discovery,2009.8(2):p.129−138;Tan,S.J.,et al.,Engineering Nanocarriers for siRNA Delivery.Small.7(7):p.841−56;Castanotto,D.and J.J.Rossi,The promises and pitfalls of RNA−interference−based therapeutics.Nature,2009.457(7228):p.426−33;Chen,Y.and L.Huang,Tumor−targeted delivery of siRNA by non−viral vector:safe and effective cancer therapy.Expert Opin Drug Deliv,2008.5(12):p.1301−11;Weinstein,S.and D.Peer,RNAi nanomedicines:challenges and opportunities within the immune system.Nanotechnology.21(23):p.232001;Fenske,D.B.and P.R.Cullis,Liposomal nanomedicines.Expert Opin Drug Deliv,2008.5(1):p.25−44;および、Thiel,K.W.and P.H.Giangrande,Therapeutic applications of DNA and RNA aptamers.Oligonucleotides,2009.19(3):p.209−22を参照のこと。現在、siRNA薬物療法学に関連する20を超える臨床治験が進行中であるか完了しており、種々の疾病の処置に対して有望な結果が示されている。例えば、Burnett,J.C.,J.J.Rossi,and K.Tiemann,Current progress of siRNA/shRNA therapeutics in clinical trials.Biotechnol J.6(9):p.1130−46を参照のこと。しかしながら、siRNAの効率的で安全な送達はいまだにsiRNA薬物療法学の開発における重要な課題である。例えば、Juliano,R.,et al.,Biological barriers to therapy with antisense and siRNA oligonucleotides.Mol Pharm,2009.6(3):p.686−95を参照のこと。
生物学的薬剤の送達効率、特異性および毒性に関連する試みを解決するために、本発明者らは、新規アミノ酸系脂質誘導体の合理的な設計および最適化を通して、広範な治療範囲を有する効力を有すると共に選択的なsiRNA送達系を開発した。
方法1.式(I)〜(III)の化合物の調製。式(i)への共役。
EtOH中のアミノ酸、ペプチドまたはポリペプチドおよび共役剤(エポキシド、チイランまたはアジリジン)の混合物(1.5:1〜3:1の共役剤対アミンの比)を、150℃のマイクロ波オーブン中で5時間照射に供した。反応混合物をフラッシュカラムクロマトグラフィーにより精製した。アミノ酸、ペプチドまたはポリペプチドが塩形態である場合には、この溶液にトリエチルアミンを添加し、照射に先立って、室温で30分間撹拌した。
アミノ酸、ペプチドまたはポリペプチドおよび共役剤(アクリレートまたはアクリルアミド)(1.5:1〜3:1のアクリレートまたは共役剤対アミン比)のエタノール(EtOH)、イソプロパノール(iPrOH)またはアセトニトリル中の混合物を90℃に加熱し、2時間〜2日間撹拌した。反応溶液をシリカゲルで濃縮し、フラッシュカラムクロマトグラフィーで精製した。
アミノ酸、ペプチドまたはポリペプチドおよび共役剤(アルデヒド)(1.5:1〜3:1のアルデヒド対アミン比)のTHFの溶液に、トリアセトキシボロヒドリドナトリウム(NaBH(OAc)3)を室温で添加した。反応混合物を室温で3日間撹拌した。反応溶液をシリカゲルで濃縮し、フラッシュカラムクロマトグラフィーで精製した。
式(IV)の化合物は、環化生成物が得られる、X1が例えば、ブロモ、クロロまたはヨードといった脱離基である活性化シュウ酸による1,2−ジアミンの縮合を介して調製され得る。式(i)、(ii)もしくは(iii)の基は、例えば、R1のアミノ側鎖置換基またはイミノ窒素族RQへの付加を介して環化後に導入され得る。例えばR2基といった骨格上の他の基は環化の前に係る導入され得る。例えば、R2は、環化前に導入される式(i)、(ii)もしくは(iii)の基であり得る。
式(V)および(VI)の化合物は、環化生成物が得られる、X1が例えば、ブロモ、クロロまたはヨードといった脱離基である活性化マロン酸による1,1−ジアミンの縮合を介して調製され得る。式(i)、(ii)もしくは(iii)の基は、例えば、R1のアミノ側鎖置換基またはイミノ窒素族RQへの付加を介して、環化後に導入され得る。例えばR2基といった骨格上の他の基は環化の前に係る導入され得る。例えば、R2は、環化前に導入される式(i)、(ii)もしくは(iii)の基であり得る。
式(VI)の化合物は、環化生成物が得られる、X1が例えば、ブロモ、クロロまたはヨードといった脱離基である活性化コハク酸によるヒドラジンの縮合を介して調製され得る。式(i)、(ii)もしくは(iii)の基は、例えば、R1のアミノ側鎖置換基またはイミノ窒素族RQへの付加を介して、環化後に導入され得る。例えばR2基といった骨格上の他の基は環化の前に係る導入され得る。例えば、R2は、環化前に導入される式(i)、(ii)もしくは(iii)の基であり得る。
実施例1.APPLの合成
スキームA〜Rに、本発明の式(I)〜(VI)のAPPLへの一般的な合成経路が示されている。これらの方法を適用することで、表4および表5に示されている多様なAPPLが生成される。
siRNA配合物
配合物A
APPL、ジステアロイルホスファチジルコリン(DSPC)、コレステロールおよびmPEG2000−DMGを、50:10:38.5:1.5のモル比で90%エタノール中に可溶化した。siRNA(対ホタルルシフェラーゼまたはfVII)を、10mMクエン酸、pH3緩衝剤中に、0.4mg/mLの濃度で可溶化させた。エタノール性脂質溶液および水性siRNA溶液をシリンジポンプによりマイクロ流体混合チャンバに送出して、siRNA−含有脂質ナノ粒子を自発的に形成させた。7:1(wt:wt)の全脂質対siRNA比で、脂質をsiRNAと組み合わせた。これらの配合物をPBSに対して透析してエタノールを除去し、緩衝剤を交換した。
マイクロ流体系混合デバイスを介して、コレステロール(Sigma−Aldrich)、DSPC(1,2−ジステアロイル−sn−グリセロ−3−ホスホコリン,Avanti)、mPEG2000−DMG(Alnylamにより合成)、および、siRNAでAPPLを配合した。例えば、Chen,D.,et al.,Rapid Discovery of Potent siRNA−Containing Lipid Nanoparticles Enabled by Controlled Microfluidic Formulation.J Am Chem Socを参照のこと。次いで、配合物を、3,500MWCO透析カセット(Pierce)において一晩かけてPBSに対して透析した。粒子を、平均粒径に係るsiRNA捕捉および動的光散乱(ZetaPALS、Brookhaven Instruments)について、改良型Ribogreenアッセイ(Invitrogen)で特徴付けた。cKK−E12配合物を、50:10:38.5:1.5のモル比で同様の方法を用いて、コレステロール、DSPCおよびmPEG2000−DMGから形成した。この配合物では、60〜70nmの粒径と、およそ65%siRNA捕捉が得られた。
ホタルルシフェラーゼおよびウミシイタケルシフェラーゼを安定して発現するHeLa細胞を、不透明で白色の96−ウェルプレート(Corning−Costar)の各ウェルに播種(14,000個の細胞/ウェル)し、一晩増殖培地に付着させた。増殖培地は、90%フェノールレッド−フリーDMEM、10%FBS、100ユニット/mlペニシリン、100mg/mlストレプトマイシン(Invitrogen)で組成した。配合した粒子の増殖培地への追加により抗ルシフェラーゼsiRNAで配合されたLNPを細胞に形質移入した。形質移入は4回反復して行った。細胞を37℃、5%CO2で1日間増殖させ、次いで、ルシフェラーゼ発現について分析した。対照例をベンダー(Invitrogen)により記載されているとおり、リポフェクタミン2000で行った。ホタルルシフェラーゼおよびウミシイタケルシフェラーゼ発現は、Dual−Gloアッセイキット(Promega)を用いて分析した。発光はVictor3ルミノメータ(Perkin Elmer)を用いて計測した。
C57BL/6マウス(Charles River Labs)をsiRNAサイレンシング実験に用いた。注入に先立って、各マウスに0.01mL/g体重の投与量で投与されるよう、配合物を、siRNA濃度でPBS中に希釈した(配列番号1(siFVIIセンス):5’−GGAucAucucAAGucuuAcT*T−3’;配列番号2(アンチセンス):5’−GuAAGAcuuGAGAuGAuccT*T−3’)。配合物を尾静脈注射を介して静脈内に投与した。48時間または72時間後、体重の増加/低減を計測し、後眼窩眼採血により血液サンプルを採取するためにイソフルオラン吸入によってマウスに麻酔をかけた。血清分離チューブ(Falcon tube,Becton Dickinson)で血清を単離し、第VII因子タンパク質レベルを色素生産性アッセイ(Biophen FVII,Aniara Corporation)により分析した。検量線をPBS−注入マウスからのサンプルを用いて作成し、相対的な第VII因子発現を、処置した群と未処置のPBS対照とを比較することにより判定した。
上記のマウスに、1mg/kgの全siRNAの投与量で配合したCy5.5−標識化siRNAを全身注入した。注射から1時間または24時間後にマウスを屠殺し;次いで、膵臓、脾臓、肝臓、腎臓、卵巣、子宮、心臓、肺および胸腺、ならびに、脂肪組織および筋肉組織の一部を取り出し、撮影した。器官を、675nmの励起波長および720nmの発光波長を用いてCaliper製のIvis imaging systemで試験した。データを、Caliper製のLiving Imageソフトウェアを用いて処理した。個々の器官のシグナル強度をすべての器官の総シグナル強度に対して規準化した。
既に報告したとおり、HeLa細胞におけるインビトロsiRNA形質移入アッセイにより、アポリタンパク質の効果を評価した。ホタルルシフェラーゼおよびウミシイタケルシフェラーゼを安定して発現するHeLa細胞を不透明で白色の96−ウェルプレート(Corning−Costar)に一晩播種した。50ngのホタル特異的siLucと共に配合したcKK−E12により細胞に形質移入し、これを4回反復した。アポリタンパク質(Fitzgerald Industries)を、細胞に加える前に、cKK−E12配合物と共に5分間インキュベートした。37℃、5%CO2で24時間インキュベーションした後、細胞を、Dual−Gloアッセイキット(Promega)を用いてルシフェラーゼ発現について分析した。細胞取り込みを可視化するために、cKK−E12をAlexa−Fluor 647−標識化siRNAと共に配合し、Hela細胞と共に3時間インキュベートした。次いで、細胞を4%パラホルムアルデヒドに固定し、0.1%サポニンで透過処理し、Hoeschtで着色した。Opera spinning disc confocal system(Perkin Elmer)を用いてすべてのイメージを撮像し、Acapellaソフトウェア(Perkin Elmer)を用いてデータを分析した。
単一アミノ酸をアルデヒド、アクリレートおよびエポキシドと反応させてAPPLを生成した。新しく合成した単一アミノ酸系脂質誘導体を、マウスにおける肝臓遺伝子のサイレンシング能について評価した。有効遺伝子標的である第VII因子(血液凝固因子)を、サイレンシングマーカーとして選択した。例えば、Akinc,A.,et al.,A combinatorial library of lipid−like materials for delivery of RNAi therapeutics.Nat Biotechnol,2008.26(5):p.561−9を参照のこと。新しい脂質誘導体を、コレステロール、DSPC、PEG−脂質およびsiRNAと共に、マイクロ流体系混合技術により配合した。例えば、Chen,D.,et al.,Rapid Discovery of Potent siRNA−Containing Lipid Nanoparticles Enabled by Controlled Microfluidic Formulation.J Am Chem Soc.を参照のこと。溶液中において不安定であるか、または、siRNAが捕捉されなかった配合物はスクリーニングを行わなかった。安定な配合物を、1mg/kgの投与量で全身投与によりマウスに注射した(図1)。この初期スクリーニングから、本発明者らは、K−E12が他のものよりも効力があることを確認した。ヒット率(50%超サイレンシング)は、60種の化合物中のものであった(すなわち、1.7%、粒子の不安定性またはsiRNAが捕捉されていないことによりスクリーニングしていない化合物も含む)。
生体内分布の研究を、裸のCy5.5で標識化したsiRNAおよび配合したcKK−E12で行った。cKK−E12配合物中の遊離siRNAによる寄与を差し引くことにより、1時間の時点で粒子の80%超が肝臓にて見出され、最も残存性のsiRNAは24時間後に腎臓を介して排出されていた(図2)。
過去の研究によれば、アポリタンパク質E(ApoE)は一定のタイプの材料について細胞取り込みおよび遺伝子サイレンシングを促進させることが可能であることが報告されている。Akinc,A.,et al.,Targeted delivery of RNAi therapeutics with endogenous and exogenous ligand−based mechanisms.Mol Ther.18(7):p.1357−64。細胞取り込みおよび遺伝子サイレンシングに対する多様なアポリタンパク質の影響をテストするために、ならびに、作用メカニズムを調べるために、cKK−E12と、ApoA、ApoB、ApoC、ApoEおよびApoHの11種のアイソフォームとで実験を行った。Hela細胞における結果によれば、ApoBを除き、ほとんどのアポリタンパク質は細胞バイアビリティに影響を与えていないことが示された。ApoA、ApoCおよびApoHは、遊離cKK−E12と比して、サイレンシングに対する顕著な影響を示さなかった(図3)。しかしながら、4種の異なるApoEアイソフォームは、ルシフェラーゼサイレンシングを顕著に向上させた。
特許請求の範囲において、「a」、「an」および「the」などの冠詞は、別段の定めがある場合、または、文脈から明白である場合を除き、1つもしくは2つ以上を意味し得る。1つの群における1つ以上の構成要素の間に「または・もしくは」を含む特許請求の範囲または記載は、別段の定めがある場合、または、文脈から明白である場合を除き、所与の生成物もしくはプロセスにおいて、前記群の構成要素の1つ、2つ以上もしくはすべてが、存在し、採用され、または、関連している場合に充足されると考えられる。本発明は、所与の生成物もしくはプロセスにおいて、前記群における正確に1つの構成要素が存在し、採用され、または、関連している実施形態を含む。本発明は、所与の生成物またはプロセスにおいて、前記群の構成要素の2つ以上もしくはすべてが存在し、採用され、または、関連している実施形態を含む。
Claims (35)
- 式(III)の化合物:
pは、1であり;
QはOであり;
R1は各場合について、独立して、
(i)水素;
(ii)C1〜10アルキル、該C 1〜10 アルキルは、ハロゲン;−OH;−OR aa ;−N(R bb ) 2 ;−SH;−SR aa 、−C(=O)R aa ;−CO 2 H;−CHO;−CO 2 R aa ;−OC(=O)R aa ;−OCO 2 R aa ;−C(=O)N(R bb ) 2 ;−OC(=O)N(R bb ) 2 ;−NR bb C(=O)R aa ;−NR bb CO 2 R aa ;−NR bb C(=O)N(R bb ) 2 ;−C(=NR bb )R aa ;−C(=NR bb )N(R bb ) 2 ;−NR bb C(=NR bb )N(R bb ) 2 ;C 3〜10 カルボシクリル;環炭素原子および、酸素、硫黄および窒素から選択される1〜4個のヘテロ環原子を有する3員〜14員ヘテロシクリル;C 6〜14 アリール;または、環炭素原子および酸素、硫黄および窒素から選択される1〜4個のヘテロ環原子を有する5員〜10員ヘテロアリールで置換されてよく、
ここで、C 3〜10 カルボシクリル、3員〜14員ヘテロシクリル、C 6〜14 アリールおよび5員〜10員ヘテロアリールは、各々独立して、0、1、2、3、4もしくは5個のR dd 基で置換されており;
R aa およびR ee は、各々独立して、C 1〜10 アルキルであり;
R bb およびR ff は、各々独立して、水素またはC 1〜10 アルキルであり;
R dd は、各々独立して、C 1〜10 アルキル、ハロゲン、−OH、−OR ee 、−N(R ff ) 2 、−SH、−SR ee 、−C(=O)R ee 、−CO 2 H、−CO 2 R ee 、−OC(=O)R ee 、−OCO 2 R ee 、−C(=O)N(R ff ) 2 、−OC(=O)N(R ff ) 2 、−NR ff C(=O)R ee 、−NR ff CO 2 R ee 、または−NR ff C(=O)N(R ff ) 2 であり;
または
(iii)式(iv)
R6およびR7の各々は、独立して、水素または式(i)もしくは(ii)の基であり、ただし、R6およびR7の少なくとも1つは式(i)または(ii)の基である)
の基であり、ただし、R1の少なくとも1つは式(iv)の基であり;
R2は各場合について、独立して、水素、または、式(i)もしくは(ii)の基であり;式(i)および(ii)は:
式(i)の基は、各場合について、独立して、式(i−a)または式(i−b)
R’は各場合について、水素であり;
Xは、O、SまたはNRXであり、式中、RXは、水素であり;
Yは、Oであり;
RPは、水素であり;
RLは、ハロゲンで置換されてよいC6〜20アルキル、またはハロゲンで置換されてよいC6〜20アルケニルであり、
ここで、特に指定しない限り、
C 1〜10 アルキルは、1〜10個の炭素原子を有する直鎖または分岐飽和炭化水素基であり、
C 1〜10 アルキレンは、二価のC 1〜10 アルキル基であり;
C 6〜20 アルキルは、6〜20個の炭素原子を有する直鎖または分岐飽和炭化水素基であり、
C 6〜20 アルケニルは、6〜20個の炭素原子、および、1つ以上の炭素−炭素二重結合を有する直鎖または分岐炭化水素基であり;
C6〜14アリールは、6〜14個の環炭素原子および0個のヘテロ原子を芳香族環系に有する6員〜14員の芳香族環系であり;
C3〜10カルボシクリルは、3〜10個の環炭素原子および0個のヘテロ原子を非芳香族環系中に有する3員〜10員の非芳香族環系であり;
ヘテロアリールは、環炭素原子および1、2、3または4個のヘテロ環原子を有する5〜10員芳香族環系であり、ただし、該芳香族環系において、ヘテロ原子は各々独立して、酸素、硫黄、窒素、ホウ素、ケイ素またはリンであり;そして
ヘテロシクリルは、環炭素原子および1、2、3または4個のヘテロ環原子を有する、3〜14員の非芳香族環系であり、各ヘテロ原子は、独立して、酸素、硫黄、窒素、ホウ素、ケイ素またはリンである)
またはその塩。 - R2の少なくとも1つが水素である、請求項1記載の化合物またはその塩。
-
R1は、−H、−CH3、−CH(CH3)2、−CH(CH3)(CH2CH3)、−CH2CH(CH3)2、
からなる群から選択され;
R 2 は各場合について、独立して、水素、または、式(i)もしくは(ii)の基であり;
式(i)および(ii)は:
式(i)の基は、各場合について、独立して、式(i−a)または式(i−b)
R’は各場合について、水素であり;
Xは、O、SまたはNR X であり、式中、R X は、水素であり;
Yは、Oであり;
R P は、水素であり;
R L は、ハロゲンで置換されてよいC 6〜20 アルキル、またはハロゲンで置換されてよいC 6〜20 アルケニルである)
からなる群から選択される、化合物またはその塩。 - R1が各々、式(iv)の基である、請求項1または2に記載の化合物またはその塩。
- RLが、ハロゲンで置換されてよいC6〜20アルキルである、請求項1〜6および7のいずれかに記載の化合物またはその塩。
- Lが、非置換のC 1〜10 アルキレンである、請求項1、2、6、9または10に記載の化合物またはその塩。
- 請求項1〜17のいずれか記載の化合物またはその塩と薬剤とを含む、医薬組成物であって、
前記薬剤が、有機小分子、有機大分子、無機小分子、無機大分子、核酸、タンパク質、ペプチド、ポリヌクレオチド、標的指向化剤、同位体標識化化学化合物、ワクチン、免疫賦活剤、免疫調節剤または、バイオプロセスにおいて有用な薬剤であり、ここで、
有機小分子は、800g/mol以下の分子量を有する有機分子であり;
有機大分子は、800g/molを超える分子量を有する有機分子であり;
無機小分子は、800g/mol以下の分子量を有する無機分子であり;
無機大分子は、800g/molを超える分子量を有する無機分子であり;
標的指向化剤は、特定の細胞を標的とする薬剤であり、抗体、抗体のフラグメント、低密度リポタンパク質(LDL)、トランスフェリン、アシアロ糖タンパク質、ヒト免疫不全ウイルスのgp120エンベロープタンパク質、炭化水素、受容体リガンド、シアル酸およびアプタマーからなる群から選択され;
免疫調節剤は、癌および/または自己免疫性疾患の処置に有用な薬剤であり;
バイオプロセスにおいて有用な薬剤は、細胞の健康および/または増殖の維持、および/または商業的に有用な化学製品または燃料の細胞によるバイオプロセシングに有用な薬剤である、
医薬組成物。 - 増殖性疾患、炎症性疾患、自己免疫性疾患、疼痛状態、肝疾患および家族性アミロイド神経障害からなる群から選択される疾病、障害または状態の処置に使用するための、請求項18記載の医薬組成物。
- 前記組成物がコレステロールをさらに含む、請求項18または19に記載の医薬組成物。
- 前記組成物が、PEG化脂質をさらに含む、請求項18〜20のいずれかに記載の医薬組成物。
- 前記組成物が、リン脂質をさらに含む、請求項18〜21のいずれかに記載の医薬組成物。
- 前記組成物が、アポリタンパク質をさらに含む、請求項18〜22のいずれかに記載の医薬組成物。
- 前記薬剤が、ポリヌクレオチドである、請求項18〜23のいずれかに記載の医薬組成物。
- 前記ポリヌクレオチドがDNAである、請求項24に記載の医薬組成物。
- 前記ポリヌクレオチドがRNAである、請求項24に記載の医薬組成物。
- 前記RNAが、RNAi、dsRNA、siRNA、shRNA、miRNAまたはアンチセンスRNAである、請求項26に記載の医薬組成物。
- 前記ポリヌクレオチドが蛋白質またはペプチドをコードする、請求項24記載の医薬組成物。
- 化合物ライブラリをスクリーニングする方法であって、
複数の異なる請求項1〜17のいずれかに記載の化合物もしくはその塩を提供するステップ;および
前記化合物ライブラリで少なくとも1つのアッセイを行って所望の特性の在否を判定するステップであって、
該所望の特性が、ポリヌクレオチドへの結合能、ヘパリンへの結合能、小分子への結合能、タンパク質への結合能、トランスフェクション効率の向上能、および/または薬剤の細胞内送達である、ステップ;
を含む方法。 - 請求項18〜28のいずれかに記載の医薬組成物を含む、対象が罹患する疾病、障害または状態を処置するための、医薬。
- 前記疾病、障害もしくは状態が、増殖性疾患、炎症性疾患、自己免疫性疾患、疼痛状態、肝疾患および家族性アミロイド神経障害からなる群から選択される、請求項30に記載の医薬。
- 対象が罹患する疾病、障害または状態の処置用の医薬を製造するための、請求項18〜28のいずれか記載の医薬組成物の使用。
- 前記疾病、障害もしくは状態が、増殖性疾患、炎症性疾患、自己免疫性疾患、疼痛状態、肝疾患および家族性アミロイド神経障害からなる群から選択される、請求項32に記載の使用。
- ポリヌクレオチドを細胞に送達するための、請求項24に記載の医薬組成物。
- 前記ポリヌクレオチドがRNAであり、前記細胞への前記RNAの送達に際して、前記RNAが、前記生体細胞における特定の遺伝子の発現に干渉可能である、請求項34に記載の医薬組成物。
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Families Citing this family (273)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0406647A (pt) | 2003-01-06 | 2005-12-06 | Angiochem Inc | Método para transportar um composto através da barreira sanguìnea do cérebro |
CA2611944A1 (en) * | 2005-06-15 | 2006-12-28 | Massachusetts Institute Of Technology | Amine-containing lipids and uses thereof |
US9365634B2 (en) | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
JP5860698B2 (ja) | 2008-04-18 | 2016-02-16 | アンジオケム,インコーポレーテッド | パクリタキセル、パクリタキセル類似体またはパクリタキセルコンジュゲートの医薬組成物ならびに関連する調製方法および使用方法 |
US8921314B2 (en) | 2008-10-15 | 2014-12-30 | Angiochem, Inc. | Conjugates of GLP-1 agonists and uses thereof |
RU2531591C2 (ru) | 2008-10-15 | 2014-10-20 | Ангиокем Инк. | Конъюгаты этопозида и доксорубицина для доставки лекарственных средств |
EP2365962B1 (en) | 2008-11-07 | 2017-07-05 | Massachusetts Institute of Technology | Aminoalcohol lipidoids and uses thereof |
CN102307904A (zh) | 2008-12-05 | 2012-01-04 | 安吉奥开米公司 | 神经降压素或神经降压素类似物的缀合物及其用途 |
JP2012512185A (ja) | 2008-12-17 | 2012-05-31 | アンジオケム インコーポレーテッド | 膜1型マトリックス金属タンパク質阻害剤およびその使用 |
CA2759129C (en) | 2009-04-20 | 2018-12-11 | Angiochem Inc. | Treatment of ovarian cancer using an anticancer agent conjugated to an angiopep-2 analog |
AU2010268726A1 (en) | 2009-07-02 | 2012-01-19 | Angiochem Inc. | Multimeric peptide conjugates and uses thereof |
US20110244026A1 (en) | 2009-12-01 | 2011-10-06 | Braydon Charles Guild | Delivery of mrna for the augmentation of proteins and enzymes in human genetic diseases |
EP3578205A1 (en) | 2010-08-06 | 2019-12-11 | ModernaTX, Inc. | A pharmaceutical formulation comprising engineered nucleic acids and medical use thereof |
EP2609135A4 (en) | 2010-08-26 | 2015-05-20 | Massachusetts Inst Technology | POLY (BETA-AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF |
SG190679A1 (en) | 2010-10-01 | 2013-07-31 | Jason Schrum | Engineered nucleic acids and methods of use thereof |
EP2691443B1 (en) | 2011-03-28 | 2021-02-17 | Massachusetts Institute of Technology | Conjugated lipomers and uses thereof |
AU2012236099A1 (en) | 2011-03-31 | 2013-10-03 | Moderna Therapeutics, Inc. | Delivery and formulation of engineered nucleic acids |
BR112013031553A2 (pt) | 2011-06-08 | 2020-11-10 | Shire Human Genetic Therapies, Inc. | composições, mrna que codifica para uma hgla e seu uso, uso de pelo menos uma molécula de mrna e um veículo de transferência e uso de um mrna que codifica para proteína exógena |
EP4212514A1 (en) | 2011-06-08 | 2023-07-19 | Translate Bio, Inc. | Cleavable lipids |
US9464124B2 (en) | 2011-09-12 | 2016-10-11 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
SG11201401196WA (en) | 2011-10-03 | 2014-05-29 | Moderna Therapeutics Inc | Modified nucleosides, nucleotides, and nucleic acids, and uses thereof |
PE20150041A1 (es) | 2011-10-27 | 2015-01-28 | Massachusetts Inst Technology | Derivados de aminoacidos funcionalizados en la terminal n capaces de formar microesferas encapsuladoras de farmaco |
AU2012352180A1 (en) | 2011-12-16 | 2014-07-31 | Moderna Therapeutics, Inc. | Modified nucleoside, nucleotide, and nucleic acid compositions |
US9283287B2 (en) | 2012-04-02 | 2016-03-15 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of nuclear proteins |
US9192651B2 (en) | 2012-04-02 | 2015-11-24 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of secreted proteins |
US9572897B2 (en) | 2012-04-02 | 2017-02-21 | Modernatx, Inc. | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
US9303079B2 (en) | 2012-04-02 | 2016-04-05 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
US20150267192A1 (en) | 2012-06-08 | 2015-09-24 | Shire Human Genetic Therapies, Inc. | Nuclease resistant polynucleotides and uses thereof |
CA2884870C (en) | 2012-08-13 | 2022-03-29 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
US9597380B2 (en) | 2012-11-26 | 2017-03-21 | Modernatx, Inc. | Terminally modified RNA |
UA117008C2 (uk) | 2013-03-14 | 2018-06-11 | Шир Хьюман Дженетік Терапіс, Інк. | IN VITRO ТРАНСКРИБОВАНА мРНК ТА КОМПОЗИЦІЯ, ЩО ЇЇ МІСТИТЬ, ДЛЯ ЗАСТОСУВАННЯ В ЛІКУВАННІ МУКОВІСЦИДОЗУ В ССАВЦЯ |
DK2970456T3 (da) | 2013-03-14 | 2021-07-05 | Translate Bio Inc | Fremgangsmåder og sammensætninger til levering af mrna-kodede antistoffer |
EP2971010B1 (en) | 2013-03-14 | 2020-06-10 | ModernaTX, Inc. | Formulation and delivery of modified nucleoside, nucleotide, and nucleic acid compositions |
EA201591229A1 (ru) | 2013-03-14 | 2016-01-29 | Шир Хьюман Дженетик Терапис, Инк. | Способы очистки матричной рнк |
US8980864B2 (en) | 2013-03-15 | 2015-03-17 | Moderna Therapeutics, Inc. | Compositions and methods of altering cholesterol levels |
US10077439B2 (en) | 2013-03-15 | 2018-09-18 | Modernatx, Inc. | Removal of DNA fragments in mRNA production process |
WO2014179562A1 (en) | 2013-05-01 | 2014-11-06 | Massachusetts Institute Of Technology | 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof |
US20160194368A1 (en) | 2013-09-03 | 2016-07-07 | Moderna Therapeutics, Inc. | Circular polynucleotides |
WO2015034928A1 (en) | 2013-09-03 | 2015-03-12 | Moderna Therapeutics, Inc. | Chimeric polynucleotides |
EP3052106A4 (en) | 2013-09-30 | 2017-07-19 | ModernaTX, Inc. | Polynucleotides encoding immune modulating polypeptides |
MX2016004249A (es) | 2013-10-03 | 2016-11-08 | Moderna Therapeutics Inc | Polinulcleotidos que codifican el receptor de lipoproteina de baja densidad. |
EA201690576A1 (ru) * | 2013-10-22 | 2016-10-31 | Шир Хьюман Дженетик Терапис, Инк. | Липидные композиции для доставки матричной рнк |
CA2928186A1 (en) | 2013-10-22 | 2015-04-30 | Shire Human Genetic Therapies, Inc. | Mrna therapy for phenylketonuria |
CN105658800A (zh) | 2013-10-22 | 2016-06-08 | 夏尔人类遗传性治疗公司 | Mrna的cns递送及其用途 |
EP3501605B1 (en) * | 2013-10-22 | 2023-06-28 | Translate Bio, Inc. | Mrna therapy for argininosuccinate synthetase deficiency |
HUE051311T2 (hu) | 2014-03-09 | 2021-03-01 | Univ Pennsylvania | Ornitin transzkarbamiláz (TC) deficiencia kezelésében alkalmas készítmények |
JP6372118B2 (ja) * | 2014-03-18 | 2018-08-15 | 東洋インキScホールディングス株式会社 | 両性界面活性剤とその製造方法 |
RS58337B1 (sr) | 2014-03-24 | 2019-03-29 | Translate Bio Inc | Irnk terapija za lečenje očnih oboljenja |
SG10201912038TA (en) | 2014-04-23 | 2020-02-27 | Modernatx Inc | Nucleic acid vaccines |
KR102470198B1 (ko) | 2014-04-25 | 2022-11-22 | 샤이어 휴먼 지네틱 테라피즈 인크. | 메신저 rna 의 정제 방법 |
MA48050A (fr) * | 2014-05-30 | 2020-02-12 | Translate Bio Inc | Lipides biodégradables pour l'administration d'acides nucléiques |
WO2015191693A2 (en) * | 2014-06-10 | 2015-12-17 | Massachusetts Institute Of Technology | Method for gene editing |
EP3160959B1 (en) * | 2014-06-24 | 2023-08-30 | Translate Bio, Inc. | Stereochemically enriched compositions for delivery of nucleic acids |
CA2953265C (en) | 2014-07-02 | 2023-09-26 | Shire Human Genetic Therapies, Inc. | Encapsulation of messenger rna |
US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
EP3169693B1 (en) | 2014-07-16 | 2022-03-09 | ModernaTX, Inc. | Chimeric polynucleotides |
WO2016014846A1 (en) | 2014-07-23 | 2016-01-28 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of intrabodies |
WO2016025643A1 (en) | 2014-08-12 | 2016-02-18 | Massachusetts Institute Of Technology | Brush-poly(glycoamidoamine)-lipids and uses thereof |
WO2016090262A1 (en) | 2014-12-05 | 2016-06-09 | Shire Human Genetic Therapies, Inc. | Messenger rna therapy for treatment of articular disease |
CA2979695A1 (en) | 2015-03-19 | 2016-09-22 | Translate Bio, Inc. | Mrna therapy for pompe disease |
EP3939571A1 (en) | 2015-05-21 | 2022-01-19 | Ohio State Innovation Foundation | Benzene-1,3,5-tricarboxamide derivatives and uses thereof |
WO2016205367A1 (en) | 2015-06-15 | 2016-12-22 | Angiochem Inc. | Methods for the treatment of leptomeningeal carcinomatosis |
EP3310764B1 (en) | 2015-06-19 | 2023-04-19 | Massachusetts Institute of Technology | Alkenyl substituted 2,5-piperazinediones and their use in compositions for delivering an agent to a subject or cell |
US11564893B2 (en) | 2015-08-17 | 2023-01-31 | Modernatx, Inc. | Methods for preparing particles and related compositions |
CN108472355A (zh) | 2015-10-22 | 2018-08-31 | 摩登纳特斯有限公司 | 单纯疱疹病毒疫苗 |
EP3364983A4 (en) | 2015-10-22 | 2019-10-23 | ModernaTX, Inc. | VACCINES AGAINST RESPIRATORY VIRUS |
CN117731769A (zh) | 2015-10-22 | 2024-03-22 | 摩登纳特斯有限公司 | 用于水痘带状疱疹病毒(vzv)的核酸疫苗 |
MA46316A (fr) | 2015-10-22 | 2021-03-24 | Modernatx Inc | Vaccin contre le cytomégalovirus humain |
MA46023A (fr) | 2015-10-22 | 2019-07-03 | Modernatx Inc | Vaccin contre le virus de la grippe à large spectre |
KR20180096592A (ko) | 2015-10-22 | 2018-08-29 | 모더나티엑스, 인크. | 호흡기 세포융합 바이러스 백신 |
HRP20220525T1 (hr) | 2015-12-23 | 2022-05-27 | Modernatx, Inc. | Postupci uporabe polinukleotida koji kodiraju ligand ox40 |
WO2017120612A1 (en) | 2016-01-10 | 2017-07-13 | Modernatx, Inc. | Therapeutic mrnas encoding anti ctla-4 antibodies |
WO2017177169A1 (en) | 2016-04-08 | 2017-10-12 | Rana Therapeutics, Inc. | Multimeric coding nucleic acid and uses thereof |
CN115837014A (zh) | 2016-05-18 | 2023-03-24 | 摩登纳特斯有限公司 | 编码松弛素的多核苷酸 |
SI3464336T1 (sl) | 2016-06-01 | 2022-06-30 | Athira Pharma, Inc. | Spojine |
EP3842530A1 (en) | 2016-06-13 | 2021-06-30 | Translate Bio, Inc. | Messenger rna therapy for the treatment of ornithine transcarbamylase deficiency |
JP7217700B2 (ja) | 2016-09-13 | 2023-02-03 | アラーガン、インコーポレイテッド | 安定化非タンパク質クロストリジウム毒素組成物 |
JP6980780B2 (ja) | 2016-10-21 | 2021-12-15 | モデルナティーエックス, インコーポレイテッド | ヒトサイトメガロウイルスワクチン |
CA3041345A1 (en) | 2016-11-10 | 2018-05-17 | Shrirang KARVE | Improved process of preparing mrna-loaded lipid nanoparticles |
US11400109B2 (en) | 2016-11-10 | 2022-08-02 | Translate Bio, Inc. | Subcutaneous delivery of messenger RNA |
JP2020501545A (ja) | 2016-12-08 | 2020-01-23 | キュアバック アーゲー | 肝疾患の処置または予防のためのrna |
WO2018104540A1 (en) | 2016-12-08 | 2018-06-14 | Curevac Ag | Rnas for wound healing |
AU2018224843A1 (en) | 2017-02-27 | 2019-09-19 | Translate Bio, Inc. | Methods for purification of messenger RNA |
EP3585892B8 (en) | 2017-02-27 | 2022-07-13 | Translate Bio, Inc. | Methods for purification of messenger rna |
WO2018157154A2 (en) | 2017-02-27 | 2018-08-30 | Translate Bio, Inc. | Novel codon-optimized cftr mrna |
MA47824A (fr) | 2017-03-07 | 2020-01-15 | Translate Bio Inc | Administration polyanionique d'acides nucléiques |
WO2018170270A1 (en) * | 2017-03-15 | 2018-09-20 | Modernatx, Inc. | Varicella zoster virus (vzv) vaccine |
MA48047A (fr) | 2017-04-05 | 2020-02-12 | Modernatx Inc | Réduction ou élimination de réponses immunitaires à des protéines thérapeutiques administrées par voie non intraveineuse, par exemple par voie sous-cutanée |
AU2018256877B2 (en) * | 2017-04-28 | 2022-06-02 | Acuitas Therapeutics, Inc. | Novel carbonyl lipids and lipid nanoparticle formulations for delivery of nucleic acids |
EP3618871A4 (en) | 2017-05-02 | 2021-01-06 | Merck Sharp & Dohme Corp. | ANTI-LAG3 ANTIBODIES ETCO-FORMULATIONS ANTI-LAG3 ANTIBODIES AND ANTI-PD-1 ANTIBODIES |
JOP20190260A1 (ar) | 2017-05-02 | 2019-10-31 | Merck Sharp & Dohme | صيغ ثابتة لأجسام مضادة لمستقبل الموت المبرمج 1 (pd-1) وطرق استخدامها |
WO2018213476A1 (en) | 2017-05-16 | 2018-11-22 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of codon-optimized mrna encoding cftr |
EP3638215A4 (en) | 2017-06-15 | 2021-03-24 | Modernatx, Inc. | RNA FORMULATIONS |
EP3641834B1 (en) | 2017-06-19 | 2023-10-04 | Translate Bio, Inc. | Messenger rna therapy for the treatment of friedreich's ataxia |
CA3073020A1 (en) | 2017-08-16 | 2019-02-21 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
WO2019036028A1 (en) | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | LIPIDS FOR USE IN LIPID NANOPARTICULAR FORMULATIONS |
WO2019036030A1 (en) | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | LIPIDS FOR USE IN LIPID NANOPARTICLE FORMULATIONS |
JP7275111B2 (ja) | 2017-08-31 | 2023-05-17 | モデルナティエックス インコーポレイテッド | 脂質ナノ粒子の生成方法 |
TW201920234A (zh) | 2017-09-11 | 2019-06-01 | 美商領導醫療有限公司 | 類鴉片促效劑肽及其用途 |
EP3461487A1 (en) * | 2017-09-29 | 2019-04-03 | Nlife Therapeutics S.L. | Compositions and methods for the delivery of mrna to hepatic cells |
EP3697422A4 (en) * | 2017-10-17 | 2021-08-11 | Sarepta Therapeutics, Inc. | CELL-PENETANT PEPTIDES FOR ANTISENSE RELEASE |
EP3700537A4 (en) * | 2017-10-17 | 2021-08-04 | Sarepta Therapeutics, Inc. | OLIGONUCLEOTIDES-BICYCLIC PEPTIDES CONJUGATES |
BR112020008451A2 (pt) * | 2017-11-06 | 2020-12-01 | Nitto Denko Corporation | composto fusogênico, composição, composições farmacêutica e para uso na distribuição de um agente ativo, e, método para prevenir, melhorar ou tratar uma doença ou condição |
CN118291456A (zh) | 2017-12-01 | 2024-07-05 | 苏州瑞博生物技术股份有限公司 | 一种核酸、含有该核酸的组合物与缀合物及制备方法和用途 |
CN110944675B (zh) | 2017-12-01 | 2024-06-04 | 苏州瑞博生物技术股份有限公司 | 一种核酸、含有该核酸的组合物与缀合物及制备方法和用途 |
US11414661B2 (en) | 2017-12-01 | 2022-08-16 | Suzhou Ribo Life Science Co., Ltd. | Nucleic acid, composition and conjugate containing nucleic acid, preparation method therefor and use thereof |
EP3719128A4 (en) | 2017-12-01 | 2021-10-27 | Suzhou Ribo Life Science Co., Ltd. | DOUBLE STRANDED OLIGONUCLEOTIDE, COMPOSITION AND CONJUGATE WITH DOUBLE STRANDED OLIGONUCLEOTIDE, METHOD OF MANUFACTURING THEREOF AND USE THEREOF |
CA3084061A1 (en) | 2017-12-20 | 2019-06-27 | Translate Bio, Inc. | Improved composition and methods for treatment of ornithine transcarbamylase deficiency |
KR102128951B1 (ko) * | 2017-12-21 | 2020-07-01 | 탑월드(주) | 비즈왁스와 동식물성 오일을 함유하는 화장료 조성물 |
AU2018394875B2 (en) | 2017-12-29 | 2023-08-03 | Suzhou Ribo Life Science Co., Ltd. | Conjugates and preparation and use thereof |
EP3746496A1 (en) | 2018-02-02 | 2020-12-09 | Translate Bio, Inc. | Cationic polymers |
CN108467475B (zh) * | 2018-03-08 | 2020-02-14 | 山西大学 | 一种环状聚合物及其制备方法和应用 |
EP3765030A4 (en) * | 2018-03-16 | 2022-01-26 | Sarepta Therapeutics, Inc. | CHIMERIC PEPTIDES FOR ANTISENSE ADMINISTRATION |
US20210220449A1 (en) | 2018-05-15 | 2021-07-22 | Translate Bio, Inc. | Subcutaneous Delivery of Messenger RNA |
EP3794008A1 (en) | 2018-05-16 | 2021-03-24 | Translate Bio, Inc. | Ribose cationic lipids |
US20220008338A1 (en) | 2018-05-24 | 2022-01-13 | Translate Bio, Inc. | Thioester Cationic Lipids |
CN112384205B (zh) | 2018-05-30 | 2024-05-03 | 川斯勒佰尔公司 | 信使rna疫苗及其用途 |
US11547666B2 (en) | 2018-05-30 | 2023-01-10 | Translate Bio, Inc. | Cationic lipids comprising a steroidal moiety |
AU2019278985A1 (en) | 2018-05-30 | 2020-12-17 | Translate Bio, Inc. | Vitamin cationic lipids |
EP3801627A1 (en) | 2018-05-30 | 2021-04-14 | Translate Bio, Inc. | Phosphoester cationic lipids |
CN108727209A (zh) * | 2018-06-20 | 2018-11-02 | 复旦大学 | 具有n,n-二烷基亮氨酸结构的化合物及其制备方法 |
EP3810196A4 (en) | 2018-06-21 | 2022-05-04 | Merck Sharp & Dohme Corp. | CYCLIC POLYPEPTIDES FOR INHIBITION OF PCSK9 |
JOP20190150A1 (ar) | 2018-06-21 | 2019-12-21 | Merck Sharp & Dohme | مركبات مناهضة لـ pcsk9 |
WO2020009805A2 (en) | 2018-06-21 | 2020-01-09 | Merck Sharp & Dohme Corp. | Cyclic polypeptides for pcsk9 inhibition |
EP3810176A4 (en) | 2018-06-21 | 2022-05-18 | RA Pharmaceuticals, Inc. | CYCLIC POLYPEPTIDES FOR INHIBITION OF PCSK9 |
EP3810129B1 (en) | 2018-06-21 | 2023-08-16 | Merck Sharp & Dohme LLC | Pcsk9 antagonist bicyclo-compounds |
EP3810177A4 (en) | 2018-06-21 | 2022-05-11 | RA Pharmaceuticals, Inc. | CYCLIC PEPTIDES FOR PCSK9 INHIBITION |
WO2020023533A1 (en) | 2018-07-23 | 2020-01-30 | Translate Bio, Inc. | Dry power formulations for messenger rna |
JP2021534101A (ja) | 2018-08-09 | 2021-12-09 | ヴェルソー セラピューティクス, インコーポレイテッド | Ccr2及びcsf1rを標的とするためのオリゴヌクレオチド組成物ならびにその使用 |
US11918600B2 (en) | 2018-08-21 | 2024-03-05 | Suzhou Ribo Life Science Co., Ltd. | Nucleic acid, pharmaceutical composition and conjugate containing nucleic acid, and use thereof |
CA3108544A1 (en) | 2018-08-24 | 2020-02-27 | Translate Bio, Inc. | Methods for purification of messenger rna |
AU2019333042A1 (en) | 2018-08-29 | 2021-03-04 | Translate Bio, Inc. | Improved process of preparing mRNA-loaded lipid nanoparticles |
KR20210102870A (ko) | 2018-08-30 | 2021-08-20 | 테나야 테라퓨틱스, 인코포레이티드 | 미오카르딘 및 ascl1을 사용한 심장 세포 재프로그래밍 |
EP3849617A1 (en) | 2018-09-14 | 2021-07-21 | Translate Bio, Inc. | Composition and methods for treatment of methylmalonic acidemia |
US11896674B2 (en) | 2018-09-30 | 2024-02-13 | Suzhou Ribo Life Science Co., Ltd. | SiRNA conjugate, preparation method therefor and use thereof |
WO2020081933A1 (en) | 2018-10-19 | 2020-04-23 | Translate Bio, Inc. | Pumpless encapsulation of messenger rna |
US20210388338A1 (en) | 2018-11-08 | 2021-12-16 | Translate Bio, Inc. | Methods and Compositions for Messenger RNA Purification |
EP3876994A2 (en) | 2018-11-09 | 2021-09-15 | Translate Bio, Inc. | Peg lipidoid compounds |
KR20210102248A (ko) | 2018-11-09 | 2021-08-19 | 트랜슬레이트 바이오 인코포레이티드 | 에스테르, 티오에스테르, 이황화물, 및 무수물 모이어티가 삽입된 2,5-디옥소피페라진 |
US20220016265A1 (en) | 2018-11-09 | 2022-01-20 | Translate Bio, Inc. | Messenger rna therapy for treatment of ocular diseases |
WO2020097376A1 (en) | 2018-11-09 | 2020-05-14 | Translate Bio, Inc. | Multi-peg lipid compounds |
US20220096612A1 (en) | 2018-11-12 | 2022-03-31 | Translatebioinc | Methods for inducing immune tolerance |
AU2019384557A1 (en) | 2018-11-21 | 2021-06-10 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
EP3883917B1 (en) | 2018-11-21 | 2024-01-24 | Translate Bio, Inc. | Cationic lipid compounds and compositions thereof for use in the delivery of messenger rna |
CN113453707A (zh) | 2018-12-21 | 2021-09-28 | 库瑞瓦格股份公司 | 用于疟疾疫苗的rna |
EP3908597A1 (en) | 2019-01-07 | 2021-11-17 | Translate Bio, Inc. | Composition and methods for treatment of primary ciliary dyskinesia |
WO2020161342A1 (en) | 2019-02-08 | 2020-08-13 | Curevac Ag | Coding rna administered into the suprachoroidal space in the treatment of ophtalmic diseases |
WO2020214946A1 (en) | 2019-04-18 | 2020-10-22 | Translate Bio, Inc. | Cystine cationic lipids |
US20220233444A1 (en) | 2019-04-22 | 2022-07-28 | Translate Bio, Inc. | Thioester cationic lipids |
EP3962902A1 (en) | 2019-05-03 | 2022-03-09 | Translate Bio, Inc. | Di-thioester cationic lipids |
CA3140423A1 (en) | 2019-05-14 | 2020-11-19 | Translate Bio, Inc. | Improved process of preparing mrna-loaded lipid nanoparticles |
EP3976593A1 (en) | 2019-05-31 | 2022-04-06 | Translate Bio, Inc. | Macrocyclic lipids |
EP3986452A1 (en) | 2019-06-18 | 2022-04-27 | CureVac AG | Rotavirus mrna vaccine |
WO2020257716A1 (en) | 2019-06-21 | 2020-12-24 | Translate Bio, Inc. | Tricine and citric acid lipids |
WO2020257611A1 (en) | 2019-06-21 | 2020-12-24 | Translate Bio, Inc. | Cationic lipids comprising an hydroxy moiety |
JP2022541740A (ja) | 2019-07-08 | 2022-09-27 | トランスレイト バイオ, インコーポレイテッド | 改善されたmRNA装填脂質ナノ粒子、およびそれを作製するプロセス |
WO2021007515A1 (en) | 2019-07-11 | 2021-01-14 | Tenaya Therapeutics, Inc. | Cardiac cell reprogramming with micrornas and other factors |
EP4003311A1 (en) | 2019-07-23 | 2022-06-01 | Translate Bio, Inc. | Stable compositions of mrna-loaded lipid nanoparticles and processes of making |
US20220323542A1 (en) | 2019-07-30 | 2022-10-13 | Translate Bio, Inc. | TREATMENT OF CYSTIC FIBROSIS BY DELIVERY OF NEBULIZED mRNA ENCODING CFTR |
JP2022544412A (ja) | 2019-08-14 | 2022-10-18 | キュアバック アーゲー | 免疫賦活特性が減少したrna組み合わせおよび組成物 |
US11484565B2 (en) | 2019-08-30 | 2022-11-01 | Merck Sharp & Dohme Llc | PCSK9 antagonist compounds |
AU2020348376A1 (en) | 2019-09-20 | 2022-04-07 | Translate Bio, Inc. | mRNA encoding engineered CFTR |
WO2021061815A1 (en) | 2019-09-23 | 2021-04-01 | Omega Therapeutics, Inc. | COMPOSITIONS AND METHODS FOR MODULATING HEPATOCYTE NUCLEAR FACTOR 4-ALPHA (HNF4α) GENE EXPRESSION |
EP4048807A1 (en) | 2019-09-23 | 2022-08-31 | Omega Therapeutics, Inc. | Compositions and methods for modulating apolipoprotein b (apob) gene expression |
WO2021072172A1 (en) | 2019-10-09 | 2021-04-15 | Translate Bio, Inc. | Compositions, methods and uses of messenger rna |
WO2021081058A1 (en) | 2019-10-21 | 2021-04-29 | Translate Bio, Inc. | Compositions, methods and uses of messenger rna |
JP7306252B2 (ja) * | 2019-12-13 | 2023-07-11 | 東洋インキScホールディングス株式会社 | 紐状ミセル組成物および含水ゲル |
AU2020408059A1 (en) | 2019-12-20 | 2022-08-11 | Translate Bio, Inc. | Rectal delivery of messenger RNA |
JP2023508881A (ja) | 2019-12-20 | 2023-03-06 | トランスレイト バイオ, インコーポレイテッド | Mrna担持脂質ナノ粒子を調製する改善されたプロセス |
BR112022011803A2 (pt) | 2019-12-20 | 2022-08-30 | Curevac Ag | Nanopartículas de lipídio para entrega de ácidos nucleicos |
WO2021142245A1 (en) | 2020-01-10 | 2021-07-15 | Translate Bio, Inc. | Compounds, pharmaceutical compositions and methods for modulating expression of muc5b in lung cells and tissues |
WO2021156267A1 (en) | 2020-02-04 | 2021-08-12 | Curevac Ag | Coronavirus vaccine |
WO2021173840A1 (en) | 2020-02-25 | 2021-09-02 | Translate Bio, Inc. | Improved processes of preparing mrna-loaded lipid nanoparticles |
AU2021230476A1 (en) | 2020-03-02 | 2022-10-20 | Tenaya Therapeutics, Inc. | Gene vector control by cardiomyocyte-expressed microRNAs |
JP2023517326A (ja) | 2020-03-11 | 2023-04-25 | オメガ セラピューティクス, インコーポレイテッド | フォークヘッドボックスp3(foxp3)遺伝子発現をモジュレートするための組成物および方法 |
WO2021189355A1 (en) * | 2020-03-26 | 2021-09-30 | Chinese Institute For Brain Research, Beijing | Amino acid mediated gene delivery and its uses |
CA3177940A1 (en) | 2020-05-07 | 2021-11-11 | Anusha DIAS | Optimized nucleotide sequences encoding sars-cov-2 antigens |
US20230181619A1 (en) | 2020-05-07 | 2023-06-15 | Translate Bio, Inc. | Improved compositions for cftr mrna therapy |
EP4146680A1 (en) | 2020-05-07 | 2023-03-15 | Translate Bio, Inc. | Composition and methods for treatment of primary ciliary dyskinesia |
EP4149556A1 (en) | 2020-05-14 | 2023-03-22 | Translate Bio, Inc. | Peg lipidoid compounds |
EP4149425A1 (en) | 2020-05-15 | 2023-03-22 | Translate Bio, Inc. | Lipid nanoparticle formulations for mrna delivery |
EP4153224A1 (en) | 2020-05-20 | 2023-03-29 | Flagship Pioneering Innovations VI, LLC | Coronavirus antigen compositions and their uses |
EP4153223A1 (en) | 2020-05-20 | 2023-03-29 | Flagship Pioneering Innovations VI, LLC | Immunogenic compositions and uses thereof |
CN111517974A (zh) * | 2020-05-28 | 2020-08-11 | 浙江昂拓莱司生物技术有限公司 | 一种氨基酸n端烷基化衍生物及其制备方法和应用 |
EP3993828A1 (en) | 2020-05-29 | 2022-05-11 | CureVac AG | Nucleic acid based combination vaccines |
EP4158031A1 (en) | 2020-05-29 | 2023-04-05 | Flagship Pioneering Innovations VI, LLC | Trem compositions and methods relating thereto |
AU2021281453A1 (en) | 2020-05-29 | 2022-11-17 | Flagship Pioneering Innovations Vi, Llc. | Trem compositions and methods relating thereto |
WO2022006527A1 (en) | 2020-07-02 | 2022-01-06 | Maritime Therapeutics, Inc. | Compositions and methods for reverse gene therapy |
WO2022023559A1 (en) | 2020-07-31 | 2022-02-03 | Curevac Ag | Nucleic acid encoded antibody mixtures |
US11406703B2 (en) | 2020-08-25 | 2022-08-09 | Modernatx, Inc. | Human cytomegalovirus vaccine |
WO2022043551A2 (en) | 2020-08-31 | 2022-03-03 | Curevac Ag | Multivalent nucleic acid based coronavirus vaccines |
AU2021336976A1 (en) | 2020-09-03 | 2023-03-23 | Flagship Pioneering Innovations Vi, Llc | Immunogenic compositions and uses thereof |
JP2023549011A (ja) | 2020-09-15 | 2023-11-22 | ヴァーヴ・セラピューティクス,インコーポレーテッド | 遺伝子編集のための脂質製剤 |
CN116546976A (zh) | 2020-10-06 | 2023-08-04 | 翻译生物公司 | 脂质纳米颗粒的改进工艺和配制 |
US20220133631A1 (en) | 2020-10-12 | 2022-05-05 | Translate Bio, Inc. | Process of preparing ice-based lipid nanoparticles |
KR20230087536A (ko) | 2020-10-12 | 2023-06-16 | 트랜슬레이트 바이오 인코포레이티드 | Mrna-로딩된 지질 나노입자를 제조하는 개선된 프로세스 |
US11771652B2 (en) | 2020-11-06 | 2023-10-03 | Sanofi | Lipid nanoparticles for delivering mRNA vaccines |
US20220160633A1 (en) | 2020-11-09 | 2022-05-26 | Translate Bio, Inc. | Compositions for delivery of codon-optimized mrna |
AU2021386737A1 (en) | 2020-11-25 | 2023-07-13 | Translate Bio, Inc. | Stable liquid lipid nanoparticle formulations |
US11932705B2 (en) | 2020-12-18 | 2024-03-19 | Merck Sharp & Dohme Llc | Cyclic polypeptides for PCSK9 inhibition |
WO2022137133A1 (en) | 2020-12-22 | 2022-06-30 | Curevac Ag | Rna vaccine against sars-cov-2 variants |
CA3171051A1 (en) | 2020-12-22 | 2022-06-30 | Curevac Ag | Pharmaceutical composition comprising lipid-based carriers encapsulating rna for multidose administration |
BR112023012377A2 (pt) | 2020-12-23 | 2023-10-24 | Flagship Pioneering Innovations Vi Llc | Composições de trems modificadas e usos das mesmas |
CN116981692A (zh) | 2021-01-14 | 2023-10-31 | 翻译生物公司 | 递送mRNA编码的抗体的方法和组合物 |
JP2024502948A (ja) * | 2021-01-20 | 2024-01-24 | ビーム セラピューティクス インク. | ナノ材料のためのイオン化可能な脂質 |
WO2022162027A2 (en) | 2021-01-27 | 2022-08-04 | Curevac Ag | Method of reducing the immunostimulatory properties of in vitro transcribed rna |
US20240123076A1 (en) | 2021-02-08 | 2024-04-18 | The Board Of Regents Of The University Of Texas System | Unsaturated dendrimers compositions, related formulations, and methods of use thereof |
WO2022204549A1 (en) | 2021-03-25 | 2022-09-29 | Translate Bio, Inc. | Optimized nucleotide sequences encoding the extracellular domain of human ace2 protein or a portion thereof |
CN117377491A (zh) | 2021-03-26 | 2024-01-09 | 葛兰素史克生物有限公司 | 免疫原性组合物 |
EP4312988A2 (en) | 2021-03-31 | 2024-02-07 | CureVac SE | Syringes containing pharmaceutical compositions comprising rna |
AU2022246895A1 (en) | 2021-03-31 | 2023-10-19 | Flagship Pioneering Innovations V, Inc. | Thanotransmission polypeptides and their use in treating cancer |
EP4326338A1 (en) | 2021-04-19 | 2024-02-28 | Translate Bio, Inc. | Improved compositions for delivery of mrna |
CA3171589A1 (en) | 2021-05-03 | 2022-11-03 | Moritz THRAN | Improved nucleic acid sequence for cell type specific expression |
WO2022264109A1 (en) | 2021-06-18 | 2022-12-22 | Sanofi | Multivalent influenza vaccines |
EP4362920A1 (en) | 2021-07-01 | 2024-05-08 | Translate Bio, Inc. | Compositions for delivery of mrna |
EP4367242A2 (en) | 2021-07-07 | 2024-05-15 | Omega Therapeutics, Inc. | Compositions and methods for modulating secreted frizzled receptor protein 1 (sfrp1) gene expression |
EP4377457A1 (en) | 2021-07-26 | 2024-06-05 | Flagship Pioneering Innovations VI, LLC | Trem compositions and uses thereof |
EP4377331A2 (en) | 2021-07-30 | 2024-06-05 | CureVac SE | Mrnas for treatment or prophylaxis of liver diseases |
CN117940158A (zh) | 2021-09-03 | 2024-04-26 | 库瑞瓦格欧洲公司 | 用于核酸递送的包含磷脂酰丝氨酸的新型脂质纳米颗粒 |
KR20240049810A (ko) | 2021-09-03 | 2024-04-17 | 큐어백 에스이 | 핵산 전달용 신규 지질 나노입자 |
AR127073A1 (es) | 2021-09-17 | 2023-12-13 | Flagship Pioneering Innovations Vi Llc | Composiciones y métodos para producir polirribonucleótidos circulares |
CN118302155A (zh) | 2021-10-05 | 2024-07-05 | 赛诺菲 | 用于冷冻和冷冻干燥脂质纳米颗粒(lnp)的方法及其获得的lnp |
WO2023059806A1 (en) | 2021-10-06 | 2023-04-13 | Massachusetts Institute Of Technology | Lipid nanoparticles for drug delivery to microglia in the brain |
WO2023069397A1 (en) | 2021-10-18 | 2023-04-27 | Flagship Pioneering Innovations Vi, Llc | Compositions and methods for purifying polyribonucleotides |
CA3235867A1 (en) | 2021-10-22 | 2023-04-27 | Munir MOSAHEB | Mrna vaccine composition |
WO2023073228A1 (en) | 2021-10-29 | 2023-05-04 | CureVac SE | Improved circular rna for expressing therapeutic proteins |
IL312334A (en) | 2021-11-05 | 2024-06-01 | Sanofi Sa | RNA vaccine for respiratory syncytial virus |
AU2022388747A1 (en) | 2021-11-10 | 2024-06-20 | Translate Bio, Inc. | Composition and methods for treatment of primary ciliary dyskinesia |
AU2022398450A1 (en) | 2021-11-23 | 2024-06-06 | Sail Biomedicines, Inc. | A bacteria-derived lipid composition and use thereof |
WO2023096990A1 (en) | 2021-11-24 | 2023-06-01 | Flagship Pioneering Innovation Vi, Llc | Coronavirus immunogen compositions and their uses |
AU2022397300A1 (en) | 2021-11-24 | 2024-06-27 | Flagship Pioneering Innovations Vi, Llc | Immunogenic compositions and their uses |
IL312799A (en) | 2021-11-24 | 2024-07-01 | Flagship Pioneering Innovations Vi Llc | Immunogenic compositions of varicella-zoster virus and uses thereof |
CA3239417A1 (en) | 2021-11-30 | 2023-06-08 | Yvonne CHAN | Human metapneumovirus vaccines |
CA3240691A1 (en) | 2021-12-17 | 2023-06-22 | Alexandra Sophie DE BOER | Methods for enrichment of circular rna under denaturing conditions |
WO2023111262A1 (en) | 2021-12-17 | 2023-06-22 | Sanofi | Lyme disease rna vaccine |
WO2023122080A1 (en) | 2021-12-20 | 2023-06-29 | Senda Biosciences, Inc. | Compositions comprising mrna and lipid reconstructed plant messenger packs |
TW202340461A (zh) | 2021-12-22 | 2023-10-16 | 美商旗艦先鋒創新有限責任公司 | 用於純化多核糖核苷酸之組成物和方法 |
WO2023122789A1 (en) | 2021-12-23 | 2023-06-29 | Flagship Pioneering Innovations Vi, Llc | Circular polyribonucleotides encoding antifusogenic polypeptides |
WO2023141538A1 (en) * | 2022-01-20 | 2023-07-27 | Ohio State Innovation Foundation | Compositions comprising lipid compounds and methods of making and use thereof |
WO2023144193A1 (en) | 2022-01-25 | 2023-08-03 | CureVac SE | Mrnas for treatment of hereditary tyrosinemia type i |
WO2023144330A1 (en) | 2022-01-28 | 2023-08-03 | CureVac SE | Nucleic acid encoded transcription factor inhibitors |
WO2023161350A1 (en) | 2022-02-24 | 2023-08-31 | Io Biotech Aps | Nucleotide delivery of cancer therapy |
WO2023183616A1 (en) | 2022-03-25 | 2023-09-28 | Senda Biosciences, Inc. | Novel ionizable lipids and lipid nanoparticles and methods of using the same |
US20230322689A1 (en) * | 2022-04-08 | 2023-10-12 | SunVax mRNA Therapeutics Inc. | Ionizable lipid compounds and lipid nanoparticle compositions |
WO2023196634A2 (en) | 2022-04-08 | 2023-10-12 | Flagship Pioneering Innovations Vii, Llc | Vaccines and related methods |
WO2023214082A2 (en) | 2022-05-06 | 2023-11-09 | Sanofi | Signal sequences for nucleic acid vaccines |
WO2023220083A1 (en) | 2022-05-09 | 2023-11-16 | Flagship Pioneering Innovations Vi, Llc | Trem compositions and methods of use for treating proliferative disorders |
TW202409283A (zh) | 2022-05-13 | 2024-03-01 | 美商旗艦先鋒創新有限責任(Vii)公司 | 雙股dna組合物及相關方法 |
WO2023227608A1 (en) | 2022-05-25 | 2023-11-30 | Glaxosmithkline Biologicals Sa | Nucleic acid based vaccine encoding an escherichia coli fimh antigenic polypeptide |
WO2023232147A1 (zh) * | 2022-06-02 | 2023-12-07 | 厦门赛诺邦格生物科技股份有限公司 | 一种氨基酸阳离子脂质 |
WO2023250112A1 (en) | 2022-06-22 | 2023-12-28 | Flagship Pioneering Innovations Vi, Llc | Compositions of modified trems and uses thereof |
WO2024003313A1 (en) | 2022-06-30 | 2024-01-04 | Sanofi | New peptides as selective il-23 receptor antagonists |
WO2024030856A2 (en) | 2022-08-01 | 2024-02-08 | Flagship Pioneering Innovations Vii, Llc | Immunomodulatory proteins and related methods |
WO2024028492A1 (en) | 2022-08-04 | 2024-02-08 | Sanofi | Quantitative assessment of rna encapsulation |
WO2024035952A1 (en) | 2022-08-12 | 2024-02-15 | Remix Therapeutics Inc. | Methods and compositions for modulating splicing at alternative splice sites |
WO2024044108A1 (en) | 2022-08-22 | 2024-02-29 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine, Inc. | Vaccines against coronaviruses |
WO2024049979A2 (en) | 2022-08-31 | 2024-03-07 | Senda Biosciences, Inc. | Novel ionizable lipids and lipid nanoparticles and methods of using the same |
WO2024068545A1 (en) | 2022-09-26 | 2024-04-04 | Glaxosmithkline Biologicals Sa | Influenza virus vaccines |
WO2024077191A1 (en) | 2022-10-05 | 2024-04-11 | Flagship Pioneering Innovations V, Inc. | Nucleic acid molecules encoding trif and additionalpolypeptides and their use in treating cancer |
DE202023106198U1 (de) | 2022-10-28 | 2024-03-21 | CureVac SE | Impfstoff auf Nukleinsäurebasis |
WO2024097664A1 (en) | 2022-10-31 | 2024-05-10 | Flagship Pioneering Innovations Vi, Llc | Compositions and methods for purifying polyribonucleotides |
WO2024094881A1 (en) | 2022-11-04 | 2024-05-10 | Sanofi | Respiratory syncytial virus rna vaccination |
WO2024102799A1 (en) | 2022-11-08 | 2024-05-16 | Flagship Pioneering Innovations Vi, Llc | Compositions and methods for producing circular polyribonucleotides |
WO2024102434A1 (en) | 2022-11-10 | 2024-05-16 | Senda Biosciences, Inc. | Rna compositions comprising lipid nanoparticles or lipid reconstructed natural messenger packs |
WO2024112652A1 (en) | 2022-11-21 | 2024-05-30 | Translate Bio, Inc. | Compositions of dry powder formulations of messenger rna and methods of use thereof |
WO2024129988A1 (en) | 2022-12-14 | 2024-06-20 | Flagship Pioneering Innovations Vii, Llc | Compositions and methods for delivery of therapeutic agents to bone |
WO2024126809A1 (en) | 2022-12-15 | 2024-06-20 | Sanofi | Mrna encoding influenza virus-like particle |
WO2024133515A1 (en) | 2022-12-20 | 2024-06-27 | Sanofi | Rhinovirus mrna vaccine |
WO2024151583A2 (en) | 2023-01-09 | 2024-07-18 | Flagship Pioneering Innovations Vii, Llc | Vaccines and related methods |
WO2024151687A1 (en) | 2023-01-09 | 2024-07-18 | Flagship Pioneering Innovations V, Inc. | Genetic switches and their use in treating cancer |
US20240238473A1 (en) | 2023-01-09 | 2024-07-18 | Beth Israel Deaconess Medical Center, Inc. | Recombinant nucleic acid molecules and their use in wound healing |
WO2024151685A1 (en) | 2023-01-09 | 2024-07-18 | Beth Israel Deaconess Medical Center, Inc. | Recombinant nucleic acid molecules and their use in wound healing |
GB202404607D0 (en) | 2024-03-29 | 2024-05-15 | Glaxosmithkline Biologicals Sa | RNA formulation |
Family Cites Families (165)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2844629A (en) | 1956-04-25 | 1958-07-22 | American Home Prod | Fatty acid amides and derivatives thereof |
NL269967A (ja) * | 1960-10-05 | |||
DE1155118B (de) | 1961-12-30 | 1963-10-03 | Basf Ag | Verfahren zur Herstellung von am Stickstoffatom substituierten Sulfonamiden |
DE1191629B (de) * | 1962-03-16 | 1965-04-22 | Basf Ag | Fungizide Mittel |
BE642774A (ja) * | 1963-04-02 | 1964-07-22 | ||
US3542581A (en) * | 1968-11-05 | 1970-11-24 | Eastman Kodak Co | Method of de-aggregating oxonol dye-containing gelatin layers |
JPS515430B1 (ja) | 1971-05-10 | 1976-02-19 | ||
GB1361627A (en) | 1970-08-04 | 1974-07-30 | Marumo H | Detergent composition |
US4258061A (en) * | 1970-08-07 | 1981-03-24 | Pfizer Inc. | Interferon induction in animals by amines |
JPS5120639B1 (ja) * | 1971-05-10 | 1976-06-26 | ||
US4022833A (en) | 1973-02-14 | 1977-05-10 | Sterling Drug Inc. | N,N'-bridged-bis[2-alkyl-2-hydroxyethylamines] |
JPS49127908A (ja) | 1973-04-20 | 1974-12-07 | ||
JPS5123537A (ja) | 1974-04-26 | 1976-02-25 | Adeka Argus Chemical Co Ltd | Kasozaisoseibutsu |
JPS5813576B2 (ja) | 1974-12-27 | 1983-03-14 | アデカ ア−ガスカガク カブシキガイシヤ | 安定化された合成高分子組成物 |
DE2520814A1 (de) | 1975-05-09 | 1976-11-18 | Bayer Ag | Lichtstabilisierung von polyurethanen |
JPS5282910A (en) * | 1975-12-30 | 1977-07-11 | Kimio Kawakita | Detergent composition |
US4265745A (en) | 1977-05-25 | 1981-05-05 | Teijin Limited | Permselective membrane |
US4308085A (en) | 1980-07-28 | 1981-12-29 | Jenoptik Jena Gmbh | Process for the preparation of high molecular thermoplastic epoxide-amine-polyadducts |
JPS5774371A (en) * | 1980-10-27 | 1982-05-10 | Nippon Paint Co Ltd | Improver for adhesion between coating film layers and paint composition containing the same |
DE3143726C2 (de) * | 1981-11-04 | 1987-02-05 | Degussa Ag, 6000 Frankfurt | Optisch aktive Prolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
US4897355A (en) | 1985-01-07 | 1990-01-30 | Syntex (U.S.A.) Inc. | N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor |
US4762915A (en) | 1985-01-18 | 1988-08-09 | Liposome Technology, Inc. | Protein-liposome conjugates |
CA1320724C (en) | 1985-07-19 | 1993-07-27 | Koichi Kanehira | Terpene amino alcohols and medicinal uses thereof |
EP0211305B1 (en) | 1985-08-05 | 1992-07-01 | Miyoshi Yushi Kabushiki Kaisha | Metal scavenging process |
DE3616824A1 (de) | 1986-05-17 | 1987-11-19 | Schering Ag | Verwendung von haertbaren kunstharzmischungen fuer oberflaechenbeschichtungen und druckfarben und verfahren zu ihrer herstellung |
JPH07115545B2 (ja) * | 1986-08-05 | 1995-12-13 | 株式会社リコー | 可逆性感熱記録材料 |
US4720517A (en) | 1986-11-24 | 1988-01-19 | Ciba-Geigy Corporation | Compositions stabilized with N-hydroxyiminodiacetic and dipropionic acids and esters thereof |
US4873370A (en) | 1987-03-03 | 1989-10-10 | Pennzoil Products Company | Alkylene diamines for use in friction and wear reducing compositions |
US4782105A (en) * | 1987-04-10 | 1988-11-01 | Ciba-Geigy Corporation | Long chain N,N,-dialkylhydroxylamines and stabilized compositions |
JPH0832856B2 (ja) * | 1987-05-15 | 1996-03-29 | 日本ペイント株式会社 | 塗料組成物 |
JPH07116064B2 (ja) * | 1987-07-21 | 1995-12-13 | 三菱化学株式会社 | 分離剤 |
WO1990003399A1 (en) * | 1988-09-30 | 1990-04-05 | Australian Commercial Research & Development Limited | Amino acid transport proteins, amino acid analogues, assay apparatus, uses thereof for treatment and diagnosis of cancer |
ZA899436B (en) * | 1988-12-12 | 1990-08-29 | Ciba Geigy | Piperidine derivatives |
FR2645866B1 (fr) | 1989-04-17 | 1991-07-05 | Centre Nat Rech Scient | Nouvelles lipopolyamines, leur preparation et leur emploi |
JPH04225954A (ja) * | 1990-05-02 | 1992-08-14 | Yoshitomi Pharmaceut Ind Ltd | アミド化合物、その医薬用途および新規1−置換ピロリジンメチルアミン類 |
US5693338A (en) * | 1994-09-29 | 1997-12-02 | Emisphere Technologies, Inc. | Diketopiperazine-based delivery systems |
US6331318B1 (en) * | 1994-09-30 | 2001-12-18 | Emisphere Technologies Inc. | Carbon-substituted diketopiperazine delivery systems |
JPH04364112A (ja) * | 1991-06-11 | 1992-12-16 | Mitsubishi Petrochem Co Ltd | 水性液体洗浄剤組成物 |
JP2684276B2 (ja) | 1991-11-27 | 1997-12-03 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
US5352461A (en) * | 1992-03-11 | 1994-10-04 | Pharmaceutical Discovery Corporation | Self assembling diketopiperazine drug delivery system |
DE4218744C2 (de) | 1992-06-04 | 1997-11-06 | Schering Ag | Verfahren zur Herstellung von N-ß-Hxdroxyalkyl-tri-N-carboxylalkyl-1,4,7,10-tetraazacyclododecan- und N-ß-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivaten und deren Metallkomplexe |
US5334761A (en) | 1992-08-28 | 1994-08-02 | Life Technologies, Inc. | Cationic lipids |
US5380778A (en) | 1992-09-30 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Fluorochemical aminoalcohols |
JPH06211978A (ja) | 1992-10-28 | 1994-08-02 | Takeda Chem Ind Ltd | 新規ポリエーテルポリオール及びそれを用いる軟質ウレタンフォームの製造法 |
US5705188A (en) | 1993-02-19 | 1998-01-06 | Nippon Shinyaku Company, Ltd. | Drug composition containing nucleic acid copolymer |
US5624976A (en) | 1994-03-25 | 1997-04-29 | Dentsply Gmbh | Dental filling composition and method |
FR2707289B1 (fr) | 1993-07-06 | 1995-08-11 | Chemoxal Sa | Procédé de préparation d'un composé hydroxylé d'amine secondaire ou tertiaire. |
US5585391A (en) * | 1993-10-08 | 1996-12-17 | Fhj Scientific, Inc. | Hydroxyl ions as unique therapeutic agents and compounds that modulate these ions, compositions employing these agents, therapeutic methods for using such agents and processes for preparing them |
JPH09505593A (ja) | 1993-11-24 | 1997-06-03 | メガバイオス・コーポレイション | ピペラジンの両親媒性誘導体 |
US5464924A (en) | 1994-01-07 | 1995-11-07 | The Dow Chemical Company | Flexible poly(amino ethers) for barrier packaging |
FR2714830B1 (fr) | 1994-01-10 | 1996-03-22 | Rhone Poulenc Rorer Sa | Composition contenant des acides nucléiques, préparation et utilisations. |
US5885613A (en) | 1994-09-30 | 1999-03-23 | The University Of British Columbia | Bilayer stabilizing components and their use in forming programmable fusogenic liposomes |
GB9524630D0 (en) | 1994-12-24 | 1996-01-31 | Zeneca Ltd | Chemical compounds |
FR2730637B1 (fr) | 1995-02-17 | 1997-03-28 | Rhone Poulenc Rorer Sa | Composition pharmaceutique contenant des acides nucleiques, et ses utilisations |
US5830430A (en) | 1995-02-21 | 1998-11-03 | Imarx Pharmaceutical Corp. | Cationic lipids and the use thereof |
US6428771B1 (en) | 1995-05-15 | 2002-08-06 | Pharmaceutical Discovery Corporation | Method for drug delivery to the pulmonary system |
US5679852A (en) * | 1995-06-02 | 1997-10-21 | Schering Aktiengesellschaft | Process for the production of DTPA-monoamides of the central carboxylic acid and their use as pharmaceutical agents |
JPH0913066A (ja) * | 1995-06-26 | 1997-01-14 | Kao Corp | ディーゼルエンジン用潤滑油添加剤及び潤滑油組成物 |
US5728844A (en) | 1995-08-29 | 1998-03-17 | Celgene Corporation | Immunotherapeutic agents |
JPH0995691A (ja) * | 1995-09-28 | 1997-04-08 | Sony Corp | 潤滑剤およびこれを用いた磁気記録媒体 |
FR2741066B1 (fr) | 1995-11-14 | 1997-12-12 | Rhone Poulenc Rorer Sa | Nouveaux agents de transfection et leurs applications pharmaceutiques |
US6344436B1 (en) * | 1996-01-08 | 2002-02-05 | Baylor College Of Medicine | Lipophilic peptides for macromolecule delivery |
NL1003008C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
TW520297B (en) | 1996-10-11 | 2003-02-11 | Sequus Pharm Inc | Fusogenic liposome composition and method |
JPH10197978A (ja) | 1997-01-09 | 1998-07-31 | Mitsubishi Paper Mills Ltd | ハロゲン化銀写真感光材料 |
AU7173698A (en) * | 1997-05-02 | 1998-11-27 | Baylor College Of Medicine | Lipophilic and/or lytic peptides for specific delivery of nucleic acids to ce lls |
JPH115786A (ja) | 1997-06-13 | 1999-01-12 | Pola Chem Ind Inc | 新規アミノヒドロキシプロピルピペラジン誘導体 |
JPH11241095A (ja) * | 1997-08-04 | 1999-09-07 | Ajinomoto Co Inc | 頭髪化粧料組成物 |
JPH11106329A (ja) * | 1997-08-04 | 1999-04-20 | Ajinomoto Co Inc | 化粧料組成物 |
JPH1180142A (ja) | 1997-09-05 | 1999-03-26 | Pola Chem Ind Inc | ジフェニルアルキル化合物の製造法 |
AU730364B2 (en) * | 1997-09-23 | 2001-03-08 | Bristol-Myers Squibb Company | Selective cPLA2 inhibitors |
FR2774092B1 (fr) | 1998-01-26 | 2000-02-18 | Air Liquide | Procede de preparation de polyazacycloalcanes greffes sur gel de silice et utilisation des composes greffes |
DE19822602A1 (de) | 1998-05-20 | 1999-11-25 | Goldschmidt Ag Th | Verfahren zur Herstellung von Polyaminosäureestern durch Veresterung von sauren Polyaminosäuren oder Umesterung von Polyaminosäureestern |
DE19911509A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
US6696424B1 (en) | 1999-05-28 | 2004-02-24 | Vical Incorporated | Cytofectin dimers and methods of use thereof |
ES2526707T3 (es) | 1999-06-29 | 2015-01-14 | Mannkind Corporation | Purificación y estabilización de péptidos y proteínas en agentes farmacéuticos |
DE19937721A1 (de) | 1999-08-10 | 2001-02-15 | Max Planck Gesellschaft | Neue Diketopiperazine |
CA2395636A1 (en) | 1999-12-30 | 2001-07-12 | Novartis Ag | Novel colloid synthetic vectors for gene therapy |
IL138474A0 (en) | 2000-09-14 | 2001-10-31 | Epox Ltd | Highly branched water-soluble polyamine oligomers, process for their preparation and applications thereof |
USRE43612E1 (en) | 2000-10-10 | 2012-08-28 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
US7427394B2 (en) | 2000-10-10 | 2008-09-23 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
US6998115B2 (en) | 2000-10-10 | 2006-02-14 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
US7776315B2 (en) * | 2000-10-31 | 2010-08-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and additional active ingredients |
US6656977B2 (en) | 2001-07-20 | 2003-12-02 | Air Products And Chemical, Inc. | Alkyl glycidyl ether-capped polyamine foam control agents |
US7101995B2 (en) | 2001-08-27 | 2006-09-05 | Mirus Bio Corporation | Compositions and processes using siRNA, amphipathic compounds and polycations |
US6974869B2 (en) * | 2001-09-18 | 2005-12-13 | Bristol-Myers Squibb Pharma Company | Piperizinones as modulators of chemokine receptor activity |
CA2462144C (en) | 2001-09-28 | 2016-09-20 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Micro-rna molecules |
DE10207178A1 (de) | 2002-02-19 | 2003-09-04 | Novosom Ag | Komponenten für die Herstellung amphoterer Liposomen |
US20030215395A1 (en) | 2002-05-14 | 2003-11-20 | Lei Yu | Controllably degradable polymeric biomolecule or drug carrier and method of synthesizing said carrier |
US7601367B2 (en) | 2002-05-28 | 2009-10-13 | Mirus Bio Llc | Compositions and processes using siRNA, amphipathic compounds and polycations |
JP2006505644A (ja) | 2002-11-04 | 2006-02-16 | ジーイー・バイエル・シリコーンズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツトゲゼルシヤフト | 線状ポリアミノおよび/またはポリアンモニウムポリシロキサン共重合体i |
WO2004048345A2 (en) * | 2002-11-22 | 2004-06-10 | Novo Nordisk A/S | 2,5-diketopiperazines for the treatment of obesity |
US6998508B2 (en) | 2003-03-10 | 2006-02-14 | Air Products And Chemicals, Inc. | Tertiary alkanolamines containing surface active alkyl groups |
US6781537B1 (en) | 2003-06-10 | 2004-08-24 | Nortel Networks Limited | High speed digital to analog converter |
WO2005007810A2 (en) | 2003-06-16 | 2005-01-27 | Grinstaff Mark W | Functional synthetic molecules and macromolecules for gene delivery |
US20050123596A1 (en) | 2003-09-23 | 2005-06-09 | Kohane Daniel S. | pH-triggered microparticles |
PL1737899T3 (pl) | 2004-04-20 | 2016-01-29 | Dendritic Nanotechnologies Inc | Polimery dendrytyczne o ulepszonej amplifikacji i wewnętrznych grupach funkcyjnych |
US7799565B2 (en) | 2004-06-07 | 2010-09-21 | Protiva Biotherapeutics, Inc. | Lipid encapsulated interfering RNA |
US20060035893A1 (en) * | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
MX2007002189A (es) | 2004-08-23 | 2008-01-11 | Mannkind Corp | Sales de dicetopiperazina, sales de dicetomorfolina o sales de dicetodioxano para suministro de farmacos. |
DE102004043342A1 (de) | 2004-09-08 | 2006-03-09 | Bayer Materialscience Ag | Blockierte Polyurethan-Prepolymere als Klebstoffe |
GB0502482D0 (en) | 2005-02-07 | 2005-03-16 | Glaxo Group Ltd | Novel compounds |
PT1854789E (pt) * | 2005-02-23 | 2013-10-23 | Shionogi & Co | Derivado de quinazolina possuindo actividade inibidora de tirosina-cinase |
WO2006105043A2 (en) | 2005-03-28 | 2006-10-05 | Dendritic Nanotechnologies, Inc. | Janus dendrimers and dendrons |
CA2611944A1 (en) | 2005-06-15 | 2006-12-28 | Massachusetts Institute Of Technology | Amine-containing lipids and uses thereof |
RU2394550C2 (ru) | 2005-09-14 | 2010-07-20 | Маннкайнд Корпорейшн | Способ получения лекарственной композиции, основанный на увеличении сродства поверхностей кристаллических микрочастиц к активным агентам |
WO2007073489A2 (en) | 2005-12-22 | 2007-06-28 | Trustees Of Boston University | Molecules for gene delivery and gene therapy, and methods of use thereof |
CN100569877C (zh) | 2005-12-30 | 2009-12-16 | 财团法人工业技术研究院 | 含多uv交联反应基的分枝状结构化合物及其应用 |
ES2647080T3 (es) | 2006-02-22 | 2017-12-19 | Mannkind Corporation | Un método para mejorar las propiedades farmacéuticas de micropartículas que comprenden dicetopiperazina y un agente activo |
KR20090041360A (ko) * | 2006-02-27 | 2009-04-28 | 테크니쉐 유니베르시테트 뮌헨 | 암 영상화 및 치료방법 |
US20070275923A1 (en) | 2006-05-25 | 2007-11-29 | Nastech Pharmaceutical Company Inc. | CATIONIC PEPTIDES FOR siRNA INTRACELLULAR DELIVERY |
CA2654302A1 (en) | 2006-06-05 | 2007-12-13 | Massachusetts Institute Of Technology | Crosslinked, degradable polymers and uses thereof |
ES2293834B1 (es) * | 2006-07-20 | 2009-02-16 | Consejo Superior Investig. Cientificas | Compuesto con actividad inhibidora de las interacciones ubc13-uev, composiciones farmaceuticas que lo comprenden y sus aplicaciones terapeuticas. |
US8071082B2 (en) | 2006-07-21 | 2011-12-06 | Massachusetts Institute Of Technology | End-modified poly(beta-amino esters) and uses thereof |
CA2667211A1 (en) | 2006-11-01 | 2008-05-08 | Pronova Biopharma Norge As | Alpha-substituted omega-3 lipids that are activators or modulators of the peroxisome proliferators-activated receptor (ppar) |
WO2008092091A2 (en) | 2007-01-26 | 2008-07-31 | Jenrin Discovery | Mao inhibiting n-benzyl-n-propargyl-amines useful for treating obesity |
EP2139461A2 (en) | 2007-03-20 | 2010-01-06 | Recepticon Aps | Amino derivatives to prevent nephrotoxicity and cancer |
JP5186126B2 (ja) | 2007-03-29 | 2013-04-17 | 公益財団法人地球環境産業技術研究機構 | 新規トリアジン誘導体ならびにその製法およびそのガス分離膜としての用途 |
US8678686B2 (en) | 2007-05-01 | 2014-03-25 | Pgr-Solutions | Multi-chain lipophilic polyamines |
JP5446119B2 (ja) * | 2007-05-08 | 2014-03-19 | 公立大学法人大阪府立大学 | 低級アシル基含有ポリアミドアミンデンドロン脂質 |
EP2195314B1 (en) | 2007-08-27 | 2011-03-23 | Theravance, Inc. | Disubstituted alkyl-8-azabicyclo [3.2.1.]octane compounds as mu opioid receptor antagonists |
GB0716897D0 (en) * | 2007-08-30 | 2007-10-10 | Univ Muenchen Tech | Cancer imaging and treatment |
JP2009087966A (ja) | 2007-09-27 | 2009-04-23 | Fujifilm Corp | 金属用研磨液及びそれを用いた研磨方法 |
NZ584048A (en) | 2007-10-02 | 2012-08-31 | Marina Biotech Inc | Lipopeptides for delivery of nucleic acids |
US9028874B2 (en) | 2008-01-03 | 2015-05-12 | Cedars-Sinai Medical Center | Antioxidant nanosphere comprising [1,2]-dithiolane moieties |
WO2009102325A1 (en) | 2008-02-13 | 2009-08-20 | Bristol-Myers Squibb Company | Imidazolyl biphenyl imidazoles as hepatitis c virus inhibitors |
DE102008013500A1 (de) * | 2008-03-10 | 2009-09-17 | Evonik Degussa Gmbh | Neue chirale Selektoren und stationäre Phasen zur Trennung von Enantiomerengemischen |
CN102245590B (zh) | 2008-10-09 | 2014-03-19 | 泰米拉制药公司 | 改善的氨基脂质和递送核酸的方法 |
US20100112042A1 (en) | 2008-10-16 | 2010-05-06 | Mdrna, Inc. | Processes and Compositions for Liposomal and Efficient Delivery of Gene Silencing Therapeutics |
WO2010062322A2 (en) | 2008-10-27 | 2010-06-03 | Massachusetts Institute Of Technology | Modulation of the immune response |
EP2365962B1 (en) | 2008-11-07 | 2017-07-05 | Massachusetts Institute of Technology | Aminoalcohol lipidoids and uses thereof |
SG172380A1 (en) * | 2008-12-26 | 2011-07-28 | Nof Corp | Arginine derivative and cosmetic comprising same |
US8314106B2 (en) * | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
JP5788806B2 (ja) * | 2008-12-29 | 2015-10-07 | マンカインド コーポレイション | 薬物送達剤用置換ジケトピペラジン及びその塩、これらを含む治療用組成物、微粒子組成物及び乾燥粉末組成物、並びに、その調整方法 |
US8835368B2 (en) * | 2009-02-18 | 2014-09-16 | The Lubrizol Corporation | Compounds and a method of lubricating an internal combustion engine |
US20100222489A1 (en) | 2009-02-27 | 2010-09-02 | Jiang Dayue D | Copolymer composition, membrane article, and methods thereof |
WO2010114789A1 (en) | 2009-04-02 | 2010-10-07 | The Siemon Company | Telecommunications patch panel |
WO2010129709A1 (en) | 2009-05-05 | 2010-11-11 | Alnylam Pharmaceuticals, Inc. | Lipid compositions |
US20120196923A1 (en) | 2009-05-15 | 2012-08-02 | Kaushal Rege | Polymers for delivering a substance into a cell |
KR20180036807A (ko) * | 2009-06-12 | 2018-04-09 | 맨카인드 코포레이션 | 한정된 비표면적을 갖는 디케토피페라진 마이크로입자 |
TR201907804T4 (tr) * | 2009-07-30 | 2019-06-21 | Spiral Therapeutics Inc | Apaf-1 inhibitör bileşikleri. |
US20110244026A1 (en) | 2009-12-01 | 2011-10-06 | Braydon Charles Guild | Delivery of mrna for the augmentation of proteins and enzymes in human genetic diseases |
GB0921871D0 (en) * | 2009-12-15 | 2010-01-27 | Univ Leuven Kath | Novel antifungal compounds |
US20110257431A1 (en) * | 2010-03-18 | 2011-10-20 | Basf Se | Process for producing side product-free aminocarboxylates |
CN101863544B (zh) | 2010-06-29 | 2011-09-28 | 湖南科技大学 | 一种氰尿酸基重金属螯合絮凝剂及其制备方法 |
EP2609135A4 (en) | 2010-08-26 | 2015-05-20 | Massachusetts Inst Technology | POLY (BETA-AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF |
KR101591153B1 (ko) | 2010-12-20 | 2016-02-02 | 그렌마크 파머수티칼스 에스. 아. | Trpa1 길항제로서의 2-아미노-4-아릴티아졸 화합물 |
EP2691443B1 (en) | 2011-03-28 | 2021-02-17 | Massachusetts Institute of Technology | Conjugated lipomers and uses thereof |
WO2012133737A1 (ja) | 2011-03-31 | 2012-10-04 | 公益財団法人地球環境産業技術研究機構 | 架橋性アミン化合物、該化合物を用いた高分子膜及びその製造方法 |
EP2532649B1 (en) | 2011-06-07 | 2015-04-08 | Incella GmbH | Amino lipids, their synthesis and uses thereof |
BR112013031553A2 (pt) | 2011-06-08 | 2020-11-10 | Shire Human Genetic Therapies, Inc. | composições, mrna que codifica para uma hgla e seu uso, uso de pelo menos uma molécula de mrna e um veículo de transferência e uso de um mrna que codifica para proteína exógena |
EP4212514A1 (en) | 2011-06-08 | 2023-07-19 | Translate Bio, Inc. | Cleavable lipids |
JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
CL2014000988A1 (es) | 2011-10-20 | 2014-11-03 | Oryzon Genomics Sa | Compuestos derivados de (aril o heteroaril) ciclopropilamida, inhibidores de lsd1; procedimiento para prepararlos; composicion farmaceutica que los comprende; y metodo para tratar o prevenir cancer, una enfermedad neurologica, una infeccion viral y la reactivacion viral despues de la latencia. |
PE20150041A1 (es) | 2011-10-27 | 2015-01-28 | Massachusetts Inst Technology | Derivados de aminoacidos funcionalizados en la terminal n capaces de formar microesferas encapsuladoras de farmaco |
CA2884870C (en) | 2012-08-13 | 2022-03-29 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
JP5991937B2 (ja) | 2013-03-06 | 2016-09-14 | Jxエネルギー株式会社 | 摩擦調整剤および潤滑油組成物 |
DK2970456T3 (da) | 2013-03-14 | 2021-07-05 | Translate Bio Inc | Fremgangsmåder og sammensætninger til levering af mrna-kodede antistoffer |
WO2014179562A1 (en) | 2013-05-01 | 2014-11-06 | Massachusetts Institute Of Technology | 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof |
US9895443B2 (en) | 2013-06-26 | 2018-02-20 | Massachusetts Institute Of Technology | Multi-tailed lipids and uses thereof |
KR101355583B1 (ko) | 2013-10-04 | 2014-01-24 | 한국지질자원연구원 | 간이 유용광물 분리 장치 및 이를 이용한 유용광물 분리 방법 |
EA201690576A1 (ru) | 2013-10-22 | 2016-10-31 | Шир Хьюман Дженетик Терапис, Инк. | Липидные композиции для доставки матричной рнк |
CN105658800A (zh) | 2013-10-22 | 2016-06-08 | 夏尔人类遗传性治疗公司 | Mrna的cns递送及其用途 |
US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
EP3310764B1 (en) | 2015-06-19 | 2023-04-19 | Massachusetts Institute of Technology | Alkenyl substituted 2,5-piperazinediones and their use in compositions for delivering an agent to a subject or cell |
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