CA2747182C - Method of making small liposomes - Google Patents
Method of making small liposomes Download PDFInfo
- Publication number
- CA2747182C CA2747182C CA2747182A CA2747182A CA2747182C CA 2747182 C CA2747182 C CA 2747182C CA 2747182 A CA2747182 A CA 2747182A CA 2747182 A CA2747182 A CA 2747182A CA 2747182 C CA2747182 C CA 2747182C
- Authority
- CA
- Canada
- Prior art keywords
- liposomes
- stream
- organic solvent
- water
- mixture
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 137
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002632 lipids Chemical class 0.000 claims abstract description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000003960 organic solvent Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 238000001816 cooling Methods 0.000 claims abstract description 29
- 239000002245 particle Substances 0.000 claims abstract description 21
- 238000002156 mixing Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 102100034256 Mucin-1 Human genes 0.000 claims description 17
- 108010008707 Mucin-1 Proteins 0.000 claims description 16
- 150000001413 amino acids Chemical group 0.000 claims description 12
- 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 9
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 8
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 5
- WKJDWDLHIOUPPL-JSOSNVBQSA-N (2s)-2-amino-3-({[(2r)-2,3-bis(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCC WKJDWDLHIOUPPL-JSOSNVBQSA-N 0.000 claims description 4
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 claims description 4
- YFWHNAWEOZTIPI-DIPNUNPCSA-N 1,2-dioctadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC YFWHNAWEOZTIPI-DIPNUNPCSA-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
- OZSITQMWYBNPMW-GDLZYMKVSA-N 1,2-ditetradecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC OZSITQMWYBNPMW-GDLZYMKVSA-N 0.000 claims description 4
- NEZDNQCXEZDCBI-UHFFFAOYSA-N 2-azaniumylethyl 2,3-di(tetradecanoyloxy)propyl phosphate Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC NEZDNQCXEZDCBI-UHFFFAOYSA-N 0.000 claims description 4
- KLFKZIQAIPDJCW-HTIIIDOHSA-N Dipalmitoylphosphatidylserine Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC KLFKZIQAIPDJCW-HTIIIDOHSA-N 0.000 claims description 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 4
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 4
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 claims description 4
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 4
- 239000012867 bioactive agent Substances 0.000 claims description 4
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims description 4
- 229960005160 dimyristoylphosphatidylglycerol Drugs 0.000 claims description 4
- BPHQZTVXXXJVHI-AJQTZOPKSA-N ditetradecanoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-AJQTZOPKSA-N 0.000 claims description 4
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 4
- 150000003904 phospholipids Chemical class 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 229930182558 Sterol Natural products 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 150000003432 sterols Chemical class 0.000 claims description 3
- 235000003702 sterols Nutrition 0.000 claims description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 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 2
- 235000004400 serine Nutrition 0.000 claims 1
- 150000003355 serines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 39
- 239000002904 solvent Substances 0.000 description 31
- 239000007788 liquid Substances 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229960005486 vaccine Drugs 0.000 description 4
- 108010028921 Lipopeptides Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010069020 alanyl-prolyl-glycine Proteins 0.000 description 3
- 108010087924 alanylproline Proteins 0.000 description 3
- 210000004899 c-terminal region Anatomy 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000013595 glycosylation Effects 0.000 description 3
- 238000006206 glycosylation reaction Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BSYKSCBTTQKOJG-GUBZILKMSA-N Arg-Pro-Ala Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(O)=O BSYKSCBTTQKOJG-GUBZILKMSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SFECXGVELZFBFJ-VEVYYDQMSA-N Pro-Asp-Thr Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O SFECXGVELZFBFJ-VEVYYDQMSA-N 0.000 description 2
- DXTOOBDIIAJZBJ-BQBZGAKWSA-N Pro-Gly-Ser Chemical compound [H]N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CO)C(O)=O DXTOOBDIIAJZBJ-BQBZGAKWSA-N 0.000 description 2
- LVHHEVGYAZGXDE-KDXUFGMBSA-N Thr-Ala-Pro Chemical compound C[C@H]([C@@H](C(=O)N[C@@H](C)C(=O)N1CCC[C@@H]1C(=O)O)N)O LVHHEVGYAZGXDE-KDXUFGMBSA-N 0.000 description 2
- FWTFAZKJORVTIR-VZFHVOOUSA-N Thr-Ser-Ala Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(O)=O FWTFAZKJORVTIR-VZFHVOOUSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000007373 indentation Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229940035032 monophosphoryl lipid a Drugs 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ALRXDIKPRCRYAU-UHFFFAOYSA-N 2-methylpropan-2-ol Chemical compound CC(C)(C)O.CC(C)(C)O ALRXDIKPRCRYAU-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- OKEWAFFWMHBGPT-XPUUQOCRSA-N Ala-His-Gly Chemical compound OC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](N)C)CC1=CN=CN1 OKEWAFFWMHBGPT-XPUUQOCRSA-N 0.000 description 1
- OLVCTPPSXNRGKV-GUBZILKMSA-N Ala-Pro-Pro Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(O)=O)CCC1 OLVCTPPSXNRGKV-GUBZILKMSA-N 0.000 description 1
- MJJIHRWNWSQTOI-VEVYYDQMSA-N Asp-Thr-Arg Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O MJJIHRWNWSQTOI-VEVYYDQMSA-N 0.000 description 1
- LCRDMSSAKLTKBU-ZDLURKLDSA-N Gly-Ser-Thr Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H](CO)NC(=O)CN LCRDMSSAKLTKBU-ZDLURKLDSA-N 0.000 description 1
- AFMOTCMSEBITOE-YEPSODPASA-N Gly-Val-Thr Chemical compound NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O AFMOTCMSEBITOE-YEPSODPASA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- NTXIJPDAHXSHNL-ONGXEEELSA-N His-Gly-Val Chemical compound [H]N[C@@H](CC1=CNC=N1)C(=O)NCC(=O)N[C@@H](C(C)C)C(O)=O NTXIJPDAHXSHNL-ONGXEEELSA-N 0.000 description 1
- 101001133056 Homo sapiens Mucin-1 Proteins 0.000 description 1
- 108010063954 Mucins Proteins 0.000 description 1
- FCCBQBZXIAZNIG-LSJOCFKGSA-N Pro-Ala-His Chemical compound C[C@H](NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](Cc1cnc[nH]1)C(O)=O FCCBQBZXIAZNIG-LSJOCFKGSA-N 0.000 description 1
- CGBYDGAJHSOGFQ-LPEHRKFASA-N Pro-Ala-Pro Chemical compound C[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)NC(=O)[C@@H]2CCCN2 CGBYDGAJHSOGFQ-LPEHRKFASA-N 0.000 description 1
- ABSSTGUCBCDKMU-UWVGGRQHSA-N Pro-Lys-Gly Chemical compound NCCCC[C@@H](C(=O)NCC(O)=O)NC(=O)[C@@H]1CCCN1 ABSSTGUCBCDKMU-UWVGGRQHSA-N 0.000 description 1
- KDBHVPXBQADZKY-GUBZILKMSA-N Pro-Pro-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 KDBHVPXBQADZKY-GUBZILKMSA-N 0.000 description 1
- BRKHVZNDAOMAHX-BIIVOSGPSA-N Ser-Ala-Pro Chemical compound C[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)NC(=O)[C@H](CO)N BRKHVZNDAOMAHX-BIIVOSGPSA-N 0.000 description 1
- XJDMUQCLVSCRSJ-VZFHVOOUSA-N Ser-Thr-Ala Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C)C(O)=O XJDMUQCLVSCRSJ-VZFHVOOUSA-N 0.000 description 1
- PZTZYZUTCPZWJH-FXQIFTODSA-N Val-Ser-Ser Chemical compound CC(C)[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)O)N PZTZYZUTCPZWJH-FXQIFTODSA-N 0.000 description 1
- 108010070944 alanylhistidine Proteins 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 108010060035 arginylproline Proteins 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004401 flow injection analysis Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 108010037850 glycylvaline Proteins 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 description 1
- 125000003473 lipid group Chemical group 0.000 description 1
- 230000029226 lipidation Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/775—Apolipopeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- A61K38/1735—Mucins, e.g. human intestinal mucin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1277—Preparation processes; Proliposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Marine Sciences & Fisheries (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US13835308P | 2008-12-17 | 2008-12-17 | |
| US61/138,353 | 2008-12-17 | ||
| PCT/US2009/068499 WO2010078045A2 (en) | 2008-12-17 | 2009-12-17 | Method of making small liposomes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2747182A1 CA2747182A1 (en) | 2010-07-08 |
| CA2747182C true CA2747182C (en) | 2014-11-18 |
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| CA2747182A Expired - Fee Related CA2747182C (en) | 2008-12-17 | 2009-12-17 | Method of making small liposomes |
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| US (3) | US20120034294A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2367532A4 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2012512260A (cg-RX-API-DMAC7.html) |
| KR (1) | KR101452033B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN102256595A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2009333177B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0923001A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2747182C (cg-RX-API-DMAC7.html) |
| EA (1) | EA020604B1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2011006562A (cg-RX-API-DMAC7.html) |
| SG (1) | SG172257A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2010078045A2 (cg-RX-API-DMAC7.html) |
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| TW201204410A (en) * | 2004-04-01 | 2012-02-01 | Oncothyreon Inc | Mucinous glycoprotein (MUC-1) vaccine |
| JP5771366B2 (ja) * | 2009-09-02 | 2015-08-26 | 株式会社バイオメッドコア | リポソーム製造装置及び方法 |
| BR112013021779A2 (pt) | 2011-02-24 | 2017-09-19 | Oncothyreon Inc | vacina de glicolipopeptídeo baseada em muc1 com adjuvante. |
| KR101387575B1 (ko) * | 2012-08-10 | 2014-04-23 | 서울대학교산학협력단 | 인지질 및 아세틸렌기를 포함하는 리포좀 및 그의 용도 |
| US9693958B2 (en) * | 2013-03-15 | 2017-07-04 | Cureport, Inc. | Methods and devices for preparation of lipid nanoparticles |
| CN105555297A (zh) * | 2013-10-02 | 2016-05-04 | 小利兰斯坦福大学托管委员会 | Wnt组合物及纯化方法 |
| US10632072B2 (en) * | 2015-03-19 | 2020-04-28 | University Of Connecticut | Systems and methods for continuous manufacturing of liposomal drug formulations |
| JP6942376B2 (ja) * | 2017-04-13 | 2021-09-29 | 国立大学法人北海道大学 | 流路構造体およびこれを用いた脂質粒子ないしミセル形成方法 |
| CA3133858A1 (en) | 2019-03-19 | 2020-09-24 | Arcturus Therapeutics, Inc. | Method of making lipid-encapsulated rna nanoparticles |
| EP3711749A1 (en) * | 2019-03-19 | 2020-09-23 | Polymun Scientific Immunbiologische Forschung GmbH | Method of making lipid nanoparticles |
| EP4401706A1 (en) | 2021-09-14 | 2024-07-24 | ADVAPHARM GmbH | Novel lipopeptide formulation |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11139961A (ja) * | 1997-11-06 | 1999-05-25 | Taisho Pharmaceut Co Ltd | リポソームの製造方法 |
| CA2318556A1 (en) * | 1998-01-16 | 1999-07-22 | Biomira, Inc. | Lipomatrix preparation |
| AU769357B2 (en) * | 1999-07-15 | 2004-01-22 | University Of British Columbia, The | Methods for preparation of lipid-encapsulated therapeutic agents |
| EP1232168B1 (en) * | 1999-11-15 | 2011-08-03 | Oncothyreon Inc. | Synthetic lipid-a analogs and uses thereof |
| US20020160039A1 (en) * | 2000-12-01 | 2002-10-31 | Biomira U.S.A., Inc. | Preparation of large liposomes by infusion into peg |
| US20030235610A1 (en) * | 2002-06-21 | 2003-12-25 | Piedmont Pharmaceuticals, Llc | Liposomes containing biologically active compounds |
| US7595195B2 (en) * | 2003-02-11 | 2009-09-29 | The Regents Of The University Of California | Microfluidic devices for controlled viscous shearing and formation of amphiphilic vesicles |
| US9198645B2 (en) * | 2003-11-26 | 2015-12-01 | The United States of America, as represented by the Secretary of Commerce of The National Institute of Standards and Technology | Controlled vesicle self-assembly in continuous two phase flow microfluidic channels |
| TW201204410A (en) * | 2004-04-01 | 2012-02-01 | Oncothyreon Inc | Mucinous glycoprotein (MUC-1) vaccine |
| US20090028931A1 (en) * | 2005-01-28 | 2009-01-29 | Bc Cancer Agency | Liposomal compositions for parenteral delivery of agents |
| DK1896051T3 (en) * | 2005-06-28 | 2015-01-05 | Oncothyreon Inc | PROCESS FOR THE TREATMENT OF PATIENTS WITH A mucinous glycoprotein (MUC1) vaccine |
| CN101267805A (zh) * | 2005-07-27 | 2008-09-17 | 普洛体维生物治疗公司 | 制造脂质体的系统和方法 |
| US20080089927A1 (en) * | 2006-04-06 | 2008-04-17 | Vladimir Malinin | Methods for Coacervation Induced Liposomal Encapsulation and Formulations Thereof |
| US7811603B2 (en) * | 2006-05-09 | 2010-10-12 | The Regents Of The University Of California | Microfluidic device for forming monodisperse lipoplexes |
| JP5126874B2 (ja) * | 2007-05-21 | 2013-01-23 | 国立大学法人神戸大学 | リポソーム製剤の製造方法 |
-
2009
- 2009-12-17 CN CN2009801509533A patent/CN102256595A/zh active Pending
- 2009-12-17 CN CN201610381865.6A patent/CN105935352A/zh active Pending
- 2009-12-17 MX MX2011006562A patent/MX2011006562A/es active IP Right Grant
- 2009-12-17 EP EP09836955A patent/EP2367532A4/en not_active Withdrawn
- 2009-12-17 BR BRPI0923001A patent/BRPI0923001A2/pt not_active IP Right Cessation
- 2009-12-17 JP JP2011542440A patent/JP2012512260A/ja active Pending
- 2009-12-17 CA CA2747182A patent/CA2747182C/en not_active Expired - Fee Related
- 2009-12-17 KR KR1020117015492A patent/KR101452033B1/ko not_active Expired - Fee Related
- 2009-12-17 SG SG2011044831A patent/SG172257A1/en unknown
- 2009-12-17 EA EA201100829A patent/EA020604B1/ru not_active IP Right Cessation
- 2009-12-17 AU AU2009333177A patent/AU2009333177B2/en not_active Ceased
- 2009-12-17 WO PCT/US2009/068499 patent/WO2010078045A2/en not_active Ceased
- 2009-12-17 US US13/140,786 patent/US20120034294A1/en not_active Abandoned
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2013
- 2013-03-13 US US13/799,324 patent/US20130330398A1/en not_active Abandoned
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2014
- 2014-07-14 JP JP2014143840A patent/JP5895030B2/ja not_active Expired - Fee Related
-
2015
- 2015-05-12 US US14/710,484 patent/US20150315217A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN105935352A (zh) | 2016-09-14 |
| AU2009333177B2 (en) | 2013-09-19 |
| US20120034294A1 (en) | 2012-02-09 |
| US20150315217A1 (en) | 2015-11-05 |
| JP2014224127A (ja) | 2014-12-04 |
| CN102256595A (zh) | 2011-11-23 |
| SG172257A1 (en) | 2011-07-28 |
| KR20110094114A (ko) | 2011-08-19 |
| AU2009333177A1 (en) | 2011-07-07 |
| BRPI0923001A2 (pt) | 2018-09-18 |
| JP5895030B2 (ja) | 2016-03-30 |
| JP2012512260A (ja) | 2012-05-31 |
| MX2011006562A (es) | 2011-09-27 |
| EA201100829A1 (ru) | 2012-02-28 |
| EP2367532A4 (en) | 2012-12-12 |
| US20130330398A1 (en) | 2013-12-12 |
| EP2367532A2 (en) | 2011-09-28 |
| WO2010078045A2 (en) | 2010-07-08 |
| KR101452033B1 (ko) | 2014-10-21 |
| WO2010078045A3 (en) | 2010-10-28 |
| CA2747182A1 (en) | 2010-07-08 |
| EA020604B1 (ru) | 2014-12-30 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20171218 |