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    • 3. 发明申请
    • COMPOUNDS FOR CHROMATOGRAPHIC SEPARATION OF RARE EARTH ELEMENTS AND S-, P-, D-METALS, METHOD OF SEPARATION, AND USE THEREOF
    • US20220259119A1
    • 2022-08-18
    • US17616340
    • 2020-05-28
    • USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I
    • Miloslav Polasek
    • C07B59/00C07D401/06C07F9/6524C07D401/14B01D15/42
    • The present invention relates to compounds of general formula (I), wherein —X is selected from a group consisting of H; C1 to C6, alkyl; halogen (F, Cl, Br or I); Y is selected from a group consisting of nitrogen; N-oxide; Z1, Z2, Zm, wherein m is 1 or 2, are independently selected from the group consisting of —CH2—CH2— and —CH2—CH2—CH24 A, Am, wherein m is 1 or 2, are independently selected from H; —CH2COOH; —CH2C(O)NH2; —CH2P(O)(OH)2, and n is 1 or 2; R1, R2, R3 are independently H; C1 to C6, alkyl; C1 to C6 alkyloxy; C6 to C10 aryloxy; benzyloxy; C1 to C6 alkylthio; C6, to C10 arylthio; F; Cl; Br; I; OH; SH; NH2; C1 to C6, alkylamino; di(C1 to C6, alkyl)amino; C1 to C6 acylamino; di(C1 to C6 acyl) amino; C6 to C10 arylamino; di(C6 to C10 aryl)amino; CN; OH; nitro; COORn, C(O)NHRn, C(O)N(Rn)2, wherein Rn is independently H or C1 to C10 alkyl or C6, to C10 aryl; and/or neighboring two of R1, R2, R3 together with neighboring two carbon atoms of the aromatic cycle form a six-membered ring, optionally substituted with one or more substituents independently selected from the group consisting of OH, SH, CF3, F, Cl, Br, I, C1 to C6, alkyl, C1to C6, alkyloxy, C1 to C6 alkylthio, NH2, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, NO2, COOH, COORn, C(O)NHRn, C(O)N(Rn)2, wherein Rn is WO 2020/244686 A1 independently H or C1 to C10 alkyl or C6 to C10 aryl; with the proviso that when n is 2 and all of Z1, Z2, Zm are —CH2—CH2—, then A is not —CH2COOH; for chromatographic separation of rare earth elements and/or s-, p- and d-block metals, as well as to the method of the separation of rare earth elements.
    • 9. 发明公开
    • 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 CIGLERKlara GRANTZ SASKOVAVaclav VANEKZuzana HEJDANKOVALenka LOUKOTOVAPavel SVECAnastasiia PRISSSilvia PETREZSELYOVA
    • A61K48/00A61K8/42A61K9/127A61K9/51C07C233/62C07C237/10C07D207/12C07D311/00C12N15/88
    • A61K48/0033A61K8/42A61K9/1271A61K9/5123C07C233/62C07C237/10C07D207/12C07D311/00C12N15/88C07C2601/14
    • 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.