CA2246568C - Phosphatidyl oligoglycerols - Google Patents
Phosphatidyl oligoglycerols Download PDFInfo
- Publication number
- CA2246568C CA2246568C CA002246568A CA2246568A CA2246568C CA 2246568 C CA2246568 C CA 2246568C CA 002246568 A CA002246568 A CA 002246568A CA 2246568 A CA2246568 A CA 2246568A CA 2246568 C CA2246568 C CA 2246568C
- Authority
- CA
- Canada
- Prior art keywords
- liposomes
- formula
- compounds
- mol
- phospholipids
- 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 - Lifetime
Links
- 125000001095 phosphatidyl group Chemical group 0.000 title description 12
- 239000002502 liposome Substances 0.000 claims abstract description 127
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 150000003904 phospholipids Chemical class 0.000 claims description 49
- 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 45
- 150000002632 lipids Chemical class 0.000 claims description 37
- -1 alkyl phospholipids Chemical class 0.000 claims description 36
- 229940079593 drug Drugs 0.000 claims description 35
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 27
- 235000012000 cholesterol Nutrition 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 230000026731 phosphorylation Effects 0.000 claims description 13
- 238000006366 phosphorylation reaction Methods 0.000 claims description 13
- 150000005846 sugar alcohols Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000000707 stereoselective effect Effects 0.000 claims description 6
- 230000001131 transforming effect Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
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- 229910019213 POCl3 Inorganic materials 0.000 claims 1
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 210000004369 blood Anatomy 0.000 abstract description 10
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- 235000013350 formula milk Nutrition 0.000 description 100
- 229940067631 phospholipid Drugs 0.000 description 54
- 125000006239 protecting group Chemical group 0.000 description 49
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 38
- 239000000543 intermediate Substances 0.000 description 38
- 239000000047 product Substances 0.000 description 33
- 235000019441 ethanol Nutrition 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
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- 150000001298 alcohols Chemical class 0.000 description 21
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- 239000011734 sodium Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- 229940107161 cholesterol Drugs 0.000 description 14
- 238000003776 cleavage reaction Methods 0.000 description 14
- 230000007017 scission Effects 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
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- 210000004185 liver Anatomy 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 150000004665 fatty acids Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 238000005574 benzylation reaction Methods 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical class OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229940022682 acetone Drugs 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
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- 235000010355 mannitol Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical class OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 229940073608 benzyl chloride Drugs 0.000 description 3
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- 150000002009 diols Chemical class 0.000 description 3
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- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
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- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 3
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 2
- VTDOEFXTVHCAAM-UHFFFAOYSA-N 4-methylpent-3-ene-1,2,3-triol Chemical compound CC(C)=C(O)C(O)CO VTDOEFXTVHCAAM-UHFFFAOYSA-N 0.000 description 2
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- KILNVBDSWZSGLL-UHFFFAOYSA-O 2-[2,3-di(hexadecanoyloxy)propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-UHFFFAOYSA-O 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene therapy
-
- 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
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
-
- 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
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Biomedical Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Plant Pathology (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19605833.3 | 1996-02-16 | ||
| DE19605833 | 1996-02-16 | ||
| DE19622224.9 | 1996-06-03 | ||
| DE19622224A DE19622224A1 (de) | 1996-02-16 | 1996-06-03 | Phosphatidyloligoglycerine |
| PCT/EP1997/000749 WO1997030058A1 (de) | 1996-02-16 | 1997-02-17 | Phosphatidyloligoglycerine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2246568A1 CA2246568A1 (en) | 1997-08-21 |
| CA2246568C true CA2246568C (en) | 2007-08-07 |
Family
ID=26022970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002246568A Expired - Lifetime CA2246568C (en) | 1996-02-16 | 1997-02-17 | Phosphatidyl oligoglycerols |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20020090383A1 (enExample) |
| EP (1) | EP0880530B1 (enExample) |
| JP (1) | JP2000506121A (enExample) |
| AT (1) | ATE244254T1 (enExample) |
| AU (1) | AU715208B2 (enExample) |
| CA (1) | CA2246568C (enExample) |
| DK (1) | DK0880530T3 (enExample) |
| ES (1) | ES2202576T3 (enExample) |
| WO (1) | WO1997030058A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19622224A1 (de) | 1996-02-16 | 1997-08-21 | Max Planck Gesellschaft | Phosphatidyloligoglycerine |
| ES2202576T3 (es) * | 1996-02-16 | 2004-04-01 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Fosfatidil-oligogliceroles. |
| EP1019417B1 (de) | 1997-08-18 | 2002-10-16 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Phospholipidanaloge verbindungen |
| DE19835611A1 (de) | 1998-08-06 | 2000-02-10 | Max Planck Gesellschaft | Neuartige Phospholipide mit synthetischen, ungesättigten Alkyl- und Acylketten |
| JP2000169520A (ja) * | 1998-10-01 | 2000-06-20 | Dai Ichi Kogyo Seiyaku Co Ltd | 新規分解型反応性乳化剤、及びこれを用いたポリマ―改質方法 |
| DE10015814A1 (de) * | 2000-03-30 | 2001-10-11 | Max Planck Gesellschaft | Arzneimittel zur Stimulierung der Leukopoese, zur Behandlung von Tumor- und Protozoenerkrankungen und Verfahren zu seiner Herstellung |
| DE10122855A1 (de) * | 2001-05-11 | 2002-11-14 | Max Planck Gesellschaft | Mittel zur Verbesserung der Gewebepenetration |
| DE10148066A1 (de) * | 2001-09-28 | 2003-04-24 | Max Planck Gesellschaft | Liposome enthaltend (Ether)-Lysolecithine |
| DE10148065A1 (de) * | 2001-09-28 | 2003-04-17 | Max Planck Gesellschaft | (Ester)-Lysolecithine in Liposomen |
| GB0205327D0 (en) * | 2002-03-06 | 2002-04-17 | Glaxo Group Ltd | compounds |
| DE10242367A1 (de) * | 2002-09-12 | 2004-03-18 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Thermolabiles Liposom mit geregelter Freigabetemperatur |
| EP2536414B1 (en) | 2010-02-18 | 2016-07-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for preventing cancer metastasis |
| US9663432B2 (en) * | 2012-12-28 | 2017-05-30 | Dow Corning Toray Co., Ltd. | High-purity monoalkenyl-containing glycerin derivative and method of manufacturing same |
| JP6501765B2 (ja) * | 2013-06-18 | 2019-04-17 | サーモソーム ゲゼルシャフト ミット べシュレンクテル ハフツングＴｈｅｒｍｏｓｏｍｅ ＧｍｂＨ | 長時間循環する刺激応答性ナノキャリア系での局所領域的治療のための立体特異性脂質 |
| CN111971066B (zh) * | 2018-01-18 | 2025-03-11 | 伊泽阿恩埃免疫疗法股份有限公司 | 脂质纳米颗粒 |
| WO2022008471A1 (en) | 2020-07-07 | 2022-01-13 | THERMOSOME GmbH | Liposome formulations |
| JPWO2022154055A1 (enExample) * | 2021-01-13 | 2022-07-21 | ||
| EP4527380A1 (en) | 2023-09-19 | 2025-03-26 | Thermosome Gmbh | Lipid nanoparticles |
| EP4527843A1 (en) | 2023-09-19 | 2025-03-26 | Thermosome Gmbh | Stereoisomeric phosphatidyloligoglycerol |
| EP4527379A1 (en) | 2023-09-19 | 2025-03-26 | Thermosome Gmbh | Lipids containing an oligoglycerol group |
| WO2025061874A1 (en) | 2023-09-19 | 2025-03-27 | THERMOSOME GmbH | Novel lipid nanoparticles |
| WO2025061835A1 (en) | 2023-09-19 | 2025-03-27 | THERMOSOME GmbH | Lipids containing an oligoglycerol group |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE240020C (enExample) | ||||
| JPS5813530A (ja) * | 1981-07-20 | 1983-01-26 | Kao Corp | ２，３−ジアルコキシプロピルグリセリルエ−テル及びその製造法並びにこれを含有する化粧料 |
| JPS6028944A (ja) * | 1983-07-25 | 1985-02-14 | Kao Corp | 新規なポリオ−ルエ−テル化合物およびその製造方法ならびにこれを含有する化粧料 |
| LU85952A1 (fr) * | 1985-06-14 | 1987-01-13 | Oreal | Nouveaux composes hemiacetaliques et leurs applications |
| DD240020A1 (de) * | 1985-08-02 | 1986-10-15 | Univ Leipzig | Verfahren zur herstellung neuer, pharmakologisch hochwirksamer phospholipide |
| US5290565A (en) * | 1989-04-06 | 1994-03-01 | L'oreal | Composition for promoting healing |
| FR2668366B1 (fr) * | 1990-10-30 | 1993-01-29 | Oreal | Utilisation cosmetique d'une composition ayant une activite antierythemale et composition correspondante. |
| JP3008131B2 (ja) | 1990-11-14 | 2000-02-14 | ロレアル | グリセリンから誘導される非イオン両親媒性化合物、その調製方法、相応する中間体化合物及び前記化合物を含有する組成物 |
| JP2898768B2 (ja) | 1991-02-25 | 1999-06-02 | 花王株式会社 | 洗浄剤組成物 |
| JPH0812519A (ja) | 1994-06-24 | 1996-01-16 | Kao Corp | 皮膚外用剤組成物 |
| ES2202576T3 (es) * | 1996-02-16 | 2004-04-01 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Fosfatidil-oligogliceroles. |
| JPH1180749A (ja) | 1997-08-29 | 1999-03-26 | Ishikawajima Harima Heavy Ind Co Ltd | 油分の分離方法およびその装置 |
-
1997
- 1997-02-17 ES ES97903308T patent/ES2202576T3/es not_active Expired - Lifetime
- 1997-02-17 EP EP97903308A patent/EP0880530B1/de not_active Expired - Lifetime
- 1997-02-17 JP JP9529011A patent/JP2000506121A/ja active Pending
- 1997-02-17 CA CA002246568A patent/CA2246568C/en not_active Expired - Lifetime
- 1997-02-17 DK DK97903308T patent/DK0880530T3/da active
- 1997-02-17 AT AT97903308T patent/ATE244254T1/de not_active IP Right Cessation
- 1997-02-17 WO PCT/EP1997/000749 patent/WO1997030058A1/de not_active Ceased
- 1997-02-17 AU AU17912/97A patent/AU715208B2/en not_active Ceased
- 1997-02-17 US US09/125,276 patent/US20020090383A1/en active Granted
- 1997-02-17 US US09/125,276 patent/US6413543B1/en not_active Expired - Lifetime
-
2002
- 2002-03-13 US US10/095,970 patent/US20030053978A1/en not_active Abandoned
-
2004
- 2004-05-07 US US10/840,607 patent/US7351428B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU715208B2 (en) | 2000-01-20 |
| US20040213836A1 (en) | 2004-10-28 |
| EP0880530A1 (de) | 1998-12-02 |
| CA2246568A1 (en) | 1997-08-21 |
| ES2202576T3 (es) | 2004-04-01 |
| DK0880530T3 (da) | 2003-10-27 |
| US7351428B2 (en) | 2008-04-01 |
| EP0880530B1 (de) | 2003-07-02 |
| US20020090383A1 (en) | 2002-07-11 |
| US6413543B1 (en) | 2002-07-02 |
| JP2000506121A (ja) | 2000-05-23 |
| WO1997030058A1 (de) | 1997-08-21 |
| AU1791297A (en) | 1997-09-02 |
| US20030053978A1 (en) | 2003-03-20 |
| ATE244254T1 (de) | 2003-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170217 |