ES2911186T3 - Formas cristalinas de aminolípidos - Google Patents
Formas cristalinas de aminolípidos Download PDFInfo
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- ES2911186T3 ES2911186T3 ES18715414T ES18715414T ES2911186T3 ES 2911186 T3 ES2911186 T3 ES 2911186T3 ES 18715414 T ES18715414 T ES 18715414T ES 18715414 T ES18715414 T ES 18715414T ES 2911186 T3 ES2911186 T3 ES 2911186T3
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- 150000003839 salts Chemical class 0.000 claims abstract description 237
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 160
- 229940125904 compound 1 Drugs 0.000 claims abstract description 147
- 239000013078 crystal Substances 0.000 claims abstract description 137
- 230000005855 radiation Effects 0.000 claims abstract description 99
- 238000002844 melting Methods 0.000 claims abstract description 19
- 230000008018 melting Effects 0.000 claims abstract description 19
- CHUGJZCCBFDAEO-UHFFFAOYSA-N heptadecan-9-yl 8-(2-hydroxyethylamino)octanoate 4-hydroxybenzoic acid Chemical group OC(=O)c1ccc(O)cc1.CCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCNCCO CHUGJZCCBFDAEO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910002483 Cu Ka Inorganic materials 0.000 claims description 96
- 229940126214 compound 3 Drugs 0.000 claims description 92
- 239000012535 impurity Substances 0.000 claims description 87
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 84
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 66
- 239000007787 solid Substances 0.000 claims description 65
- 229940125782 compound 2 Drugs 0.000 claims description 60
- 238000001757 thermogravimetry curve Methods 0.000 claims description 37
- -1 heptadecan-9-yl Chemical group 0.000 claims description 30
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 16
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 8
- GWUCYKSFGLCADO-KSLMYTHLSA-N C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.CN(CCCC(=O)OC(CCCCCCCC\C=C/C\C=C/CCCCC)CCCCCCCC\C=C/C\C=C/CCCCC)C Chemical compound C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.CN(CCCC(=O)OC(CCCCCCCC\C=C/C\C=C/CCCCC)CCCCCCCC\C=C/C\C=C/CCCCC)C GWUCYKSFGLCADO-KSLMYTHLSA-N 0.000 claims description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 5
- IYHXCYLNXNEHBV-UHFFFAOYSA-N 8-[2-hydroxyethyl-(6-oxo-6-undecoxyhexyl)amino]octanoic acid Chemical compound CCCCCCCCCCCOC(=O)CCCCCN(CCCCCCCC(=O)O)CCO IYHXCYLNXNEHBV-UHFFFAOYSA-N 0.000 claims description 3
- RFCLYIWOPYPUOK-UHFFFAOYSA-N C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.OCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCCCCCCC(=O)OCCCCCCCCC Chemical group C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.OCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCCCCCCC(=O)OCCCCCCCCC RFCLYIWOPYPUOK-UHFFFAOYSA-N 0.000 claims description 2
- NRLNQCOGCKAESA-KWXKLSQISA-N [(6z,9z,28z,31z)-heptatriaconta-6,9,28,31-tetraen-19-yl] 4-(dimethylamino)butanoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCC(OC(=O)CCCN(C)C)CCCCCCCC\C=C/C\C=C/CCCCC NRLNQCOGCKAESA-KWXKLSQISA-N 0.000 description 127
- 238000000034 method Methods 0.000 description 57
- 239000012458 free base Substances 0.000 description 52
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 46
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 39
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 27
- 230000008569 process Effects 0.000 description 25
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 23
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- 238000001907 polarising light microscopy Methods 0.000 description 20
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- 150000002632 lipids Chemical class 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- WRCUIPZUTXISRZ-UHFFFAOYSA-N heptadecan-9-yl 8-(2-hydroxyethylamino)octanoate Chemical compound OCCNCCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC WRCUIPZUTXISRZ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
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- 125000005591 trimellitate group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzothiophene Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- BGNVBNJYBVCBJH-UHFFFAOYSA-N SM-102 Chemical compound OCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCCCCC(OCCCCCCCCCCC)=O BGNVBNJYBVCBJH-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
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- 238000000746 purification Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 238000001938 differential scanning calorimetry curve Methods 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 6
- BSGJGRYCFGSRFM-UHFFFAOYSA-N 2,4-dioxo-1H-pyrimidine-6-carboxylic acid heptadecan-9-yl 8-(2-hydroxyethylamino)octanoate Chemical compound OC(=O)c1cc(=O)[nH]c(=O)[nH]1.CCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCNCCO BSGJGRYCFGSRFM-UHFFFAOYSA-N 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229960005010 orotic acid Drugs 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 108020004707 nucleic acids Proteins 0.000 description 5
- 150000007523 nucleic acids Chemical class 0.000 description 5
- 102000039446 nucleic acids Human genes 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
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- 230000001376 precipitating effect Effects 0.000 description 5
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- QCXJEYYXVJIFCE-UHFFFAOYSA-M 4-acetamidobenzoate Chemical compound CC(=O)NC1=CC=C(C([O-])=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000001351 cycling effect Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
- OXOWTLDONRGYOT-UHFFFAOYSA-M 4-(dimethylamino)butanoate Chemical compound CN(C)CCCC([O-])=O OXOWTLDONRGYOT-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960001270 d- tartaric acid Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- SKKOMNKDLZJSNH-UHFFFAOYSA-N heptadecan-9-yl 8-(2-hydroxyethylamino)octanoate sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCNCCO SKKOMNKDLZJSNH-UHFFFAOYSA-N 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- ABCVHPIKBGRCJA-UHFFFAOYSA-N nonyl 8-[(8-heptadecan-9-yloxy-8-oxooctyl)-(2-hydroxyethyl)amino]octanoate Chemical class OCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCCCCCCC(=O)OCCCCCCCCC ABCVHPIKBGRCJA-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000000935 solvent evaporation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- YONLFQNRGZXBBF-UHFFFAOYSA-N 2,3-dibenzoyloxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- NTETZVIZWIEWPA-UHFFFAOYSA-N C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.OCCNCCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC Chemical compound C(C1=CC(C(=O)O)=CC(C(=O)O)=C1)(=O)O.OCCNCCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC NTETZVIZWIEWPA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- 108020004459 Small interfering RNA Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000030279 gene silencing Effects 0.000 description 2
- 238000012226 gene silencing method Methods 0.000 description 2
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- 230000002440 hepatic effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
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- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
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- 238000003860 storage Methods 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UEDWDABYRNGIDC-UHFFFAOYSA-N 8-[2-hydroxyethyl-(8-nonoxy-8-oxooctyl)amino]octanoic acid Chemical compound OCCN(CCCCCCCC(=O)O)CCCCCCCC(=O)OCCCCCCCCC UEDWDABYRNGIDC-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000033289 adaptive immune response Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002288 cocrystallisation Methods 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- KHEPAYMMEKWSAW-UHFFFAOYSA-N heptadecan-9-yl 8-bromooctanoate Chemical compound BrCCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC KHEPAYMMEKWSAW-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Inorganic materials [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
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- 108020004999 messenger RNA Proteins 0.000 description 1
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- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 235000003702 sterols Nutrition 0.000 description 1
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- 238000004441 surface measurement Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
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- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/06—Oxalic acid
- C07C55/07—Salts thereof
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- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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| WO2018170322A1 (en) | 2018-09-20 |
| US11203569B2 (en) | 2021-12-21 |
| SI3596042T1 (sl) | 2022-04-29 |
| AU2018234814A1 (en) | 2019-09-19 |
| JP7220154B2 (ja) | 2023-02-09 |
| JP2020512316A (ja) | 2020-04-23 |
| US20220073449A1 (en) | 2022-03-10 |
| CA3056133A1 (en) | 2018-09-20 |
| US20200131116A1 (en) | 2020-04-30 |
| AU2018234814B2 (en) | 2022-06-30 |
| EP3596042B1 (en) | 2022-01-12 |
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