TW202320737A

TW202320737A - 製備用於將酬載分子遞送至氣道上皮之脂質奈米粒子組成物之製程

製備用於將酬載分子遞送至氣道上皮之脂質奈米粒子組成物之製程 Download PDF

Info

Publication number: TW202320737A
Authority: TW; Taiwan
Prior art keywords: alkyl; lipid; buffer; composition; process according
Prior art date: 2021-07-26

Application number

TW111127850A

Other languages

English (en)

Chinese (zh)

Inventor

麥可Ｈ史密斯

尼米爾素德

田暢

丹尼爾Ｗ多爾蒂

Original Assignee

美商現代公司

Priority date

2021-07-26

Filing date

2022-07-25

Publication date

2023-06-01

2022-07-25 Application filed by 美商現代公司 filed Critical 美商現代公司

2023-06-01 Publication of TW202320737A publication Critical patent/TW202320737A/zh

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150000002632 lipids Chemical class 0.000 title claims abstract description 608
239000000203 mixture Substances 0.000 title claims abstract description 489
239000002105 nanoparticle Substances 0.000 title claims abstract description 385
238000000034 method Methods 0.000 title claims abstract description 177
230000008569 process Effects 0.000 title claims abstract description 125
210000000981 epithelium Anatomy 0.000 title claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims description 224
239000000872 buffer Substances 0.000 claims description 204
239000000243 solution Substances 0.000 claims description 182
150000001875 compounds Chemical class 0.000 claims description 158
108020004999 messenger RNA Proteins 0.000 claims description 140
235000002639 sodium chloride Nutrition 0.000 claims description 128
239000003795 chemical substances by application Substances 0.000 claims description 108
150000003839 salts Chemical class 0.000 claims description 107
-1 cationic lipid Chemical class 0.000 claims description 78
125000003342 alkenyl group Chemical group 0.000 claims description 74
150000007523 nucleic acids Chemical class 0.000 claims description 67
125000002091 cationic group Chemical group 0.000 claims description 65
102000039446 nucleic acids Human genes 0.000 claims description 65
108020004707 nucleic acids Proteins 0.000 claims description 65
150000003904 phospholipids Chemical class 0.000 claims description 63
239000002577 cryoprotective agent Substances 0.000 claims description 60
239000008351 acetate buffer Substances 0.000 claims description 55
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 55
239000012062 aqueous buffer Substances 0.000 claims description 48
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 43
229930006000 Sucrose Natural products 0.000 claims description 41
239000005720 sucrose Substances 0.000 claims description 41
239000007983 Tris buffer Substances 0.000 claims description 39
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 33
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 32
150000001204 N-oxides Chemical class 0.000 claims description 32
125000003277 amino group Chemical group 0.000 claims description 30
201000010099 disease Diseases 0.000 claims description 30
239000004094 surface-active agent Substances 0.000 claims description 30
239000013024 dilution buffer Substances 0.000 claims description 29
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 28
239000007979 citrate buffer Substances 0.000 claims description 27
150000003141 primary amines Chemical class 0.000 claims description 27
150000003512 tertiary amines Chemical class 0.000 claims description 27
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 27
150000003335 secondary amines Chemical class 0.000 claims description 26
210000004027 cell Anatomy 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 22
239000011780 sodium chloride Substances 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 19
125000005647 linker group Chemical group 0.000 claims description 18
229930182558 Sterol Natural products 0.000 claims description 17
238000002156 mixing Methods 0.000 claims description 17
235000003702 sterols Nutrition 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 16
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 16
239000008363 phosphate buffer Substances 0.000 claims description 16
235000012000 cholesterol Nutrition 0.000 claims description 14
238000005538 encapsulation Methods 0.000 claims description 14
238000007865 diluting Methods 0.000 claims description 13
150000003432 sterols Chemical class 0.000 claims description 13
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 12
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 10
229910017053 inorganic salt Inorganic materials 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
230000002378 acidificating effect Effects 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
150000003431 steroids Chemical class 0.000 claims description 9
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 8
159000000000 sodium salts Chemical class 0.000 claims description 8
125000000185 sucrose group Chemical group 0.000 claims description 8
210000001552 airway epithelial cell Anatomy 0.000 claims description 7
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 6
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 6
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 6
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 6
235000000431 campesterol Nutrition 0.000 claims description 6
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 6
210000002919 epithelial cell Anatomy 0.000 claims description 6
230000002209 hydrophobic effect Effects 0.000 claims description 6
235000016831 stigmasterol Nutrition 0.000 claims description 6
229940032091 stigmasterol Drugs 0.000 claims description 6
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 6
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 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
230000002685 pulmonary effect Effects 0.000 claims description 5
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 description 5
LVNGJLRDBYCPGB-LDLOPFEMSA-N (R)-1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-LDLOPFEMSA-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
229940087168 alpha tocopherol Drugs 0.000 claims description 4
229960001231 choline Drugs 0.000 claims description 4
229960000984 tocofersolan Drugs 0.000 claims description 4
239000002076 α-tocopherol Substances 0.000 claims description 4
235000004835 α-tocopherol Nutrition 0.000 claims description 4
WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 3
BIABMEZBCHDPBV-BEBVUIBBSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphoglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-BEBVUIBBSA-N 0.000 claims description 3
YCISYUZWCSTBCY-BAYLZEKJSA-N 2-aminoethyl [(2r)-2,3-bis(3,7,11,15-tetramethylhexadecoxy)propyl] hydrogen phosphate Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CCOC[C@H](COP(O)(=O)OCCN)OCCC(C)CCCC(C)CCCC(C)CCCC(C)C YCISYUZWCSTBCY-BAYLZEKJSA-N 0.000 claims description 3
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 3
UKDDQGWMHWQMBI-SOFRWFQSSA-N [(2R)-2,3-bis(3,7,11,15-tetramethylhexadecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC(C)CCCC(C)CCCC(C)CCCC(C)C UKDDQGWMHWQMBI-SOFRWFQSSA-N 0.000 claims description 3
NMRGXROOSPKRTL-SUJDGPGCSA-N [(2r)-2,3-bis(3,7,11,15-tetramethylhexadecoxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OCCC(C)CCCC(C)CCCC(C)CCCC(C)C NMRGXROOSPKRTL-SUJDGPGCSA-N 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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 3
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 3
229940068065 phytosterols Drugs 0.000 claims description 3
REJLGAUYTKNVJM-SGXCCWNXSA-N tomatine Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@@]1(NC[C@@H](C)CC1)O5)C)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O REJLGAUYTKNVJM-SGXCCWNXSA-N 0.000 claims description 3
229940096998 ursolic acid Drugs 0.000 claims description 3
PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 3
RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims description 2
HCTYOHVVRRHDTQ-SKIDARPTSA-N (2s)-2,3-bis[(z)-octadec-9-enoxy]propan-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCOC[C@H](CO)OCCCCCCCC\C=C/CCCCCCCC HCTYOHVVRRHDTQ-SKIDARPTSA-N 0.000 claims description 2
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 2
GDYHKPCXCBYUMI-UUSMYCRBSA-N 1,2-diarachidonoyl-sn-glycero-3-phosphate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC GDYHKPCXCBYUMI-UUSMYCRBSA-N 0.000 claims description 2
DSNRWDQKZIEDDB-SQYFZQSCSA-N 1,2-dioleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC DSNRWDQKZIEDDB-SQYFZQSCSA-N 0.000 claims description 2
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 2
RTKYXZVOHQHXNA-JJDZEPKFSA-N 2-aminoethyl [(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoxy]propyl] hydrogen phosphate Chemical compound C(CCCCCCC\C=C/C\C=C/CCCCC)OC[C@@H](OCCCCCCCC\C=C/C\C=C/CCCCC)COP(=O)(O)OCCN RTKYXZVOHQHXNA-JJDZEPKFSA-N 0.000 claims description 2
SHCCKWGIFIPGNJ-NSUCVBPYSA-N 2-aminoethyl [(2r)-2,3-bis[(z)-octadec-9-enoxy]propyl] hydrogen phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC[C@H](COP(O)(=O)OCCN)OCCCCCCCC\C=C/CCCCCCCC SHCCKWGIFIPGNJ-NSUCVBPYSA-N 0.000 claims description 2
OILXMJHPFNGGTO-NRHJOKMGSA-N Brassicasterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 OILXMJHPFNGGTO-NRHJOKMGSA-N 0.000 claims description 2
GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 claims description 2
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 2
239000008777 Glycerylphosphorylcholine Substances 0.000 claims description 2
QMGSCYSTMWRURP-UHFFFAOYSA-N Tomatine Natural products CC1CCC2(NC1)OC3CC4C5CCC6CC(CCC6(C)C5CCC4(C)C3C2C)OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(O)C%10O)C8O)C(O)C7O QMGSCYSTMWRURP-UHFFFAOYSA-N 0.000 claims description 2
OILXMJHPFNGGTO-ZRUUVFCLSA-N UNPD197407 Natural products 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](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZRUUVFCLSA-N 0.000 claims description 2
GQVBSOVDJKCLGM-VCZQVZGSSA-N [(2R)-2,3-di(docosa-2,4,6,8,10,12-hexaenoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC GQVBSOVDJKCLGM-VCZQVZGSSA-N 0.000 claims description 2
UKMFPLRYBOOPKL-VHONOUADSA-N [(2R)-3-hexadecoxy-2-[(Z)-octadec-9-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OCCCCCCCC\C=C/CCCCCCCC UKMFPLRYBOOPKL-VHONOUADSA-N 0.000 claims description 2
OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol 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](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 claims description 2
235000004420 brassicasterol Nutrition 0.000 claims description 2
150000001783 ceramides Chemical class 0.000 claims description 2
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
150000001985 dialkylglycerols Chemical class 0.000 claims description 2
230000004064 dysfunction Effects 0.000 claims description 2
DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims description 2
229960004956 glycerylphosphorylcholine Drugs 0.000 claims description 2
150000002422 hopanes Chemical class 0.000 claims description 2
VLBPIWYTPAXCFJ-XMMPIXPASA-N lysophosphatidylcholine O-16:0/0:0 Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C VLBPIWYTPAXCFJ-XMMPIXPASA-N 0.000 claims description 2
150000008103 phosphatidic acids Chemical class 0.000 claims description 2
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NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 3
239000012266 salt solution Substances 0.000 claims 3
JTERLNYVBOZRHI-PPBJBQABSA-N (2-aminoethoxy)[(2r)-2,3-bis[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC JTERLNYVBOZRHI-PPBJBQABSA-N 0.000 claims 1
WIHSZOXPODIZSW-KJIWEYRQSA-N PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC WIHSZOXPODIZSW-KJIWEYRQSA-N 0.000 claims 1
QZVNWIFCXCGEQT-GWHBCOKCSA-N [(2s)-2-docosa-2,4,6,8,10,12-hexaenoyloxy-3-hydroxypropyl] docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OC[C@H](CO)OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC QZVNWIFCXCGEQT-GWHBCOKCSA-N 0.000 claims 1
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 1
QYIXCDOBOSTCEI-NWKZBHTNSA-N coprostanol Chemical compound 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-NWKZBHTNSA-N 0.000 claims 1
150000001982 diacylglycerols Chemical class 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 abstract description 32
230000000069 prophylactic effect Effects 0.000 abstract description 27
238000002360 preparation method Methods 0.000 abstract description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
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