CA3055653A1 - Lipid nanoparticle formulation - Google Patents

Info

Publication number

CA3055653A1

CA3055653A1 CA3055653A CA3055653A CA3055653A1 CA 3055653 A1 CA3055653 A1 CA 3055653A1 CA 3055653 A CA3055653 A CA 3055653A CA 3055653 A CA3055653 A CA 3055653A CA 3055653 A1 CA3055653 A1 CA 3055653A1

Authority

CA

Canada

Prior art keywords

nanoparticle composition

alkyl

group

lipid

nanoparticle

Prior art date

2017-03-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

• Espacenet
• Global Dossier
• CIPO
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• 239000000203 mixture Substances 0.000 title claims abstract description 248
• 239000002105 nanoparticle Substances 0.000 title claims abstract description 246
• 150000002632 lipids Chemical class 0.000 title claims abstract description 162
• 238000009472 formulation Methods 0.000 title description 9
• 229930182558 Sterol Natural products 0.000 claims abstract description 74
• 150000003432 sterols Chemical class 0.000 claims abstract description 74
• 235000003702 sterols Nutrition 0.000 claims abstract description 74
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 71
• 230000000069 prophylactic effect Effects 0.000 claims abstract description 69
• 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 60
• 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 60
• 229920001184 polypeptide Polymers 0.000 claims abstract description 59
• 230000014509 gene expression Effects 0.000 claims abstract description 37
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 37
• 102000004169 proteins and genes Human genes 0.000 claims abstract description 33
• 150000003904 phospholipids Chemical class 0.000 claims abstract description 30
• GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims abstract description 23
• GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims abstract description 22
• 239000011732 tocopherol Substances 0.000 claims abstract description 21
• 229960001295 tocopherol Drugs 0.000 claims abstract description 21
• 210000004962 mammalian cell Anatomy 0.000 claims abstract description 20
• 210000000056 organ Anatomy 0.000 claims abstract description 18
• 235000010384 tocopherol Nutrition 0.000 claims abstract description 18
• 229930003799 tocopherol Natural products 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 275
• 102000040430 polynucleotide Human genes 0.000 claims description 175
• 108091033319 polynucleotide Proteins 0.000 claims description 175
• 239000002157 polynucleotide Substances 0.000 claims description 175
• 239000002773 nucleotide Substances 0.000 claims description 151
• 125000003729 nucleotide group Chemical group 0.000 claims description 150
• -1 ent-cholesterol Natural products 0.000 claims description 142
• 125000000217 alkyl group Chemical group 0.000 claims description 132
• 108020004999 messenger RNA Proteins 0.000 claims description 123
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 104
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 90
• 238000000034 method Methods 0.000 claims description 86
• 210000004027 cell Anatomy 0.000 claims description 82
• 150000001841 cholesterols Chemical class 0.000 claims description 75
• 125000003342 alkenyl group Chemical group 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 229940107161 cholesterol Drugs 0.000 claims description 55
• 235000012000 cholesterol Nutrition 0.000 claims description 53
• 150000007523 nucleic acids Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 49
• 201000010099 disease Diseases 0.000 claims description 48
• 102000039446 nucleic acids Human genes 0.000 claims description 48
• 108020004707 nucleic acids Proteins 0.000 claims description 48
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 229920002477 rna polymer Polymers 0.000 claims description 44
• 208000035475 disorder Diseases 0.000 claims description 42
• 239000001257 hydrogen Substances 0.000 claims description 42
• 239000002777 nucleoside Substances 0.000 claims description 41
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• 238000001890 transfection Methods 0.000 claims description 29
• 239000003795 chemical substances by application Substances 0.000 claims description 28
• 241000124008 Mammalia Species 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 230000001965 increasing effect Effects 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
• 239000004055 small Interfering RNA Substances 0.000 claims description 22
• 230000000694 effects Effects 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 21
• 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 19
• 150000001204 N-oxides Chemical class 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
• 241000282414 Homo sapiens Species 0.000 claims description 15
• 108020004459 Small interfering RNA Proteins 0.000 claims description 15
• LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 239000004094 surface-active agent Substances 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 11
• 108091027967 Small hairpin RNA Proteins 0.000 claims description 11
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
• 230000008488 polyadenylation Effects 0.000 claims description 11
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 10
• 229940032091 stigmasterol Drugs 0.000 claims description 10
• 235000016831 stigmasterol Nutrition 0.000 claims description 10
• BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims description 9
• 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 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 9
• 125000004419 alkynylene group Chemical group 0.000 claims description 9
• 125000002091 cationic group Chemical group 0.000 claims description 9
• HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 9
• JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000002679 microRNA Substances 0.000 claims description 8
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000002904 solvent Substances 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• LRFJOIPOPUJUMI-KWXKLSQISA-N 2-[2,2-bis[(9z,12z)-octadeca-9,12-dienyl]-1,3-dioxolan-4-yl]-n,n-dimethylethanamine Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCC1(CCCCCCCC\C=C/C\C=C/CCCCC)OCC(CCN(C)C)O1 LRFJOIPOPUJUMI-KWXKLSQISA-N 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 208000035473 Communicable disease Diseases 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• 238000005538 encapsulation Methods 0.000 claims description 7
• 230000009452 underexpressoin Effects 0.000 claims description 7
• 108700011259 MicroRNAs Proteins 0.000 claims description 6
• QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 6
• 230000002018 overexpression Effects 0.000 claims description 6
• WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 6
• PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims description 6
• LDGWQMRUWMSZIU-LQDDAWAPSA-M 2,3-bis[(z)-octadec-9-enoxy]propyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCCOCC(C[N+](C)(C)C)OCCCCCCCC\C=C/CCCCCCCC LDGWQMRUWMSZIU-LQDDAWAPSA-M 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 208000026350 Inborn Genetic disease Diseases 0.000 claims description 5
• 208000035977 Rare disease Diseases 0.000 claims description 5
• HIHOWBSBBDRPDW-PTHRTHQKSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] n-[2-(dimethylamino)ethyl]carbamate Chemical compound C1C=C2C[C@@H](OC(=O)NCCN(C)C)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HIHOWBSBBDRPDW-PTHRTHQKSA-N 0.000 claims description 5
• 230000001594 aberrant effect Effects 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
• 230000003247 decreasing effect Effects 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• PSLWZOIUBRXAQW-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC PSLWZOIUBRXAQW-UHFFFAOYSA-M 0.000 claims description 5
• 208000016361 genetic disease Diseases 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 208000030159 metabolic disease Diseases 0.000 claims description 5
• XVUQPECVOGMPRU-ZPPAUJSGSA-N n,n-dimethyl-1,2-bis[(9z,12z)-octadeca-9,12-dienoxy]propan-1-amine Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCOC(C)C(N(C)C)OCCCCCCCC\C=C/C\C=C/CCCCC XVUQPECVOGMPRU-ZPPAUJSGSA-N 0.000 claims description 5
• GLGLUQVVDHRLQK-WRBBJXAJSA-N n,n-dimethyl-2,3-bis[(z)-octadec-9-enoxy]propan-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCOCC(CN(C)C)OCCCCCCCC\C=C/CCCCCCCC GLGLUQVVDHRLQK-WRBBJXAJSA-N 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 5
• 230000002062 proliferating effect Effects 0.000 claims description 5
• 208000019553 vascular disease Diseases 0.000 claims description 5
• OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 claims description 4
• QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical group C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 4
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• FVXDQWZBHIXIEJ-LNDKUQBDSA-N 1,2-di-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC FVXDQWZBHIXIEJ-LNDKUQBDSA-N 0.000 claims description 4
• KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 4
• SLKDGVPOSSLUAI-PGUFJCEWSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC SLKDGVPOSSLUAI-PGUFJCEWSA-N 0.000 claims description 4
• SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims description 4
• NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims description 4
• LVNGJLRDBYCPGB-UHFFFAOYSA-N 1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-UHFFFAOYSA-N 0.000 claims description 4
• BIABMEZBCHDPBV-MPQUPPDSSA-N 1,2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-MPQUPPDSSA-N 0.000 claims description 4
• MBZYKEVPFYHDOH-BQNIITSRSA-N 24,25-dihydrolanosterol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@]21C MBZYKEVPFYHDOH-BQNIITSRSA-N 0.000 claims description 4
• SLQKYSPHBZMASJ-QKPORZECSA-N 24-methylene-cholest-8-en-3β-ol Chemical compound C([C@@]12C)C[C@H](O)C[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCC(=C)C(C)C)CC[C@H]21 SLQKYSPHBZMASJ-QKPORZECSA-N 0.000 claims description 4
• CQSRUKJFZKVYCY-UHFFFAOYSA-N 5alpha-isofucostan-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 CQSRUKJFZKVYCY-UHFFFAOYSA-N 0.000 claims description 4
• SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims description 4
• DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims description 4
• GBBBJSKVBYJMBG-QTWVXCTBSA-N Fucosterol Natural products CC=C(CC[C@@H](C)[C@@H]1CC[C@@H]2[C@H]3C=C[C@@H]4C[C@H](O)CC[C@@]4(C)[C@@H]3CC[C@@]12C)C(C)C GBBBJSKVBYJMBG-QTWVXCTBSA-N 0.000 claims description 4
• BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims description 4
• OSELKOCHBMDKEJ-VRUYXKNBSA-N Isofucosterol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C OSELKOCHBMDKEJ-VRUYXKNBSA-N 0.000 claims description 4
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 4
• LGJMUZUPVCAVPU-JFBKYFIKSA-N Sitostanol Natural products O[C@@H]1C[C@H]2[C@@](C)([C@@H]3[C@@H]([C@H]4[C@@](C)([C@@H]([C@@H](CC[C@H](C(C)C)CC)C)CC4)CC3)CC2)CC1 LGJMUZUPVCAVPU-JFBKYFIKSA-N 0.000 claims description 4
• CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 claims description 4
• SJDMTGSQPOFVLR-UHFFFAOYSA-N [10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] tetradecanoate Chemical compound C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCCCCCCC)C2 SJDMTGSQPOFVLR-UHFFFAOYSA-N 0.000 claims description 4
• NONFBHXKNNVFMO-UHFFFAOYSA-N [2-aminoethoxy(tetradecanoyloxy)phosphoryl] tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OP(=O)(OCCN)OC(=O)CCCCCCCCCCCCC NONFBHXKNNVFMO-UHFFFAOYSA-N 0.000 claims description 4
• SLQKYSPHBZMASJ-UHFFFAOYSA-N bastadin-1 Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(C)CCC(=C)C(C)C)CCC21 SLQKYSPHBZMASJ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims description 4
• 235000000431 campesterol Nutrition 0.000 claims description 4
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• OSELKOCHBMDKEJ-JUGJNGJRSA-N fucosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC\C(=C/C)C(C)C)[C@@]1(C)CC2 OSELKOCHBMDKEJ-JUGJNGJRSA-N 0.000 claims description 4
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