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    • 1. 发明公开
      US20240335559A1 CYCLOHEXANE LIPIDOIDS FOR NUCLEIC ACID TRANSFECTION AND USE THEREOF 审中-公开
    • CYCLOHEXANE LIPIDOIDS FOR NUCLEIC ACID TRANSFECTION AND USE THEREOF
    • US20240335559A1
    • 2024-10-10
    • US18579456
    • 2022-07-15
    • USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR V.V.I.
    • Petr CIGLER , Klara GRANTZ SASKOVA , Vaclav VANEK , Zuzana HEJDANKOVA , Lenka LOUKOTOVA , Pavel SVEC , Anastasiia PRISS , Silvia PETREZSELYOVA
    • A61K48/00 , A61K8/42 , A61K9/127 , A61K9/51 , C07C233/62 , C07C237/10 , C07D207/12 , C07D311/00 , C12N15/88
    • A61K48/0033 , A61K8/42 , A61K9/1271 , A61K9/5123 , C07C233/62 , C07C237/10 , C07D207/12 , C07D311/00 , C12N15/88 , C07C2601/14
    • The present invention relates to a lipidoid of general formula I, wherein X is selected from —C(═O)NH—, —C(═O)O—, —C(═S)O—, —C(═O)S—, —C(═S)S—, —C(═O)NHNH—, —CH2—, —O—, —OC(═O)—, —S—, —SC(═O)—, —NH—, —NHNH—, —NHC(═O)—, —NHNHC(═O)—, —C═C—, —CH═CH—, a five-membered heterocycle containing at least 2 nitrogen atoms, —CH2C(═O)NH—, —CH2C(═S)O—, —CH2C(═S)S—, —CH2C(═O)NHNH—, —N═CH—, —CH═N—, —NH—N═CH—, and —CH═N—NH—; Y is alkylene C2-C10 chain; R1 is selected from alkyl C1-C46, alkenyl C2-C46, alkynyl C2-C46; Z is selected from H, —OH, —CH3, —CH2OH, —NH2, —C(═O)NH2, —CONH(CH2)2OH, —CON[(CH2)2OH]2, —CONHCH(CH2OH)2, —CONHCH2CH(—OH)CH2OH, —CONH(CH2)2C(═O)NH2, —CON[CH2C(═O)NH2]2, —CONH(CH2)2NHC(═O)NH2, —CONH(CH2)3—N+(CH3)2—(CH2)2—SO3—, —CONH(CH2)3—N+(CH3)2—(CH2)2—COO−, —COO(CH2)2—O—P(═O)(O—)—O(CH2)2—N+(CH3)3, —N+(CH3)2—(CH2)3—SO3—, —N+(CH3)2—(CH2)2—COO−, formula (II), and formula (III), wherein R2 is independently selected from hydrogen and —CH3; E is independently selected from O and S atoms; n is an integer within the range of from 1 to 5; and T is selected from —X—Y—N(R1)2, —C(═O)O(C1-C3 alkyl), —C(═O)OCH2CH2OH, formula (IV), formula (V), formula (VI), —C(═O)OH, —CONH(CH2)2OH, —CON[(CH2)2OH]2, —CONHCH(CH2OH)2, CONH(CH2)2C(═O)NH2, —CON[CH2C(═O)NH2]2, —CONHCH[C(═O)NH2]2, —CONH(CH2)2NHC(═O)NH2, —C(═O)NH2, —CONH(CH2)3—N+(CH3)2—(CH2)2—SO3—, —CONH(CH2)3—N+(CH3)2—(CH2)2—COO−, —NH2, —NHC(═O)CH3, —COO(CH2)2—O—P(═O)(O—)—O(CH2)2—N+(CH3)3, —OH, —O(C1-C3 alkyl), —NHC(═O)NH(CH3), —NHC(═S)N(CH3)2, —NHC(═S)NH(CH3), —NHC(═N—CN)NH2, —NHC(═N—CN)NH(CH3), —NHC(═N—CN)N(CH3)2, —NHC[═N—S(═O)2NH2]NH2, —N+(CH3)2—(CH2)3—SO3—, —N+(CH3)2—(CH2)2—COO−, wherein R2, E and n are as defined above; and/or if Z is —OH or —CH2OH, and T is —C(═O)OH, then Z together with T and three carbon atoms between them may form a cyclic lactone containing 4 to 5 carbon atoms; and pharmaceutically acceptable salts, addition salts and solvates thereof. This lipidoid is useful as a transfection agent. The invention further describes transfection reagents, transfection particles containing this lipidoid, and their use.
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