JP2000506121A - ホスファチジルオリゴグリセリン - Google Patents
ホスファチジルオリゴグリセリンInfo
- Publication number
- JP2000506121A JP2000506121A JP9529011A JP52901197A JP2000506121A JP 2000506121 A JP2000506121 A JP 2000506121A JP 9529011 A JP9529011 A JP 9529011A JP 52901197 A JP52901197 A JP 52901197A JP 2000506121 A JP2000506121 A JP 2000506121A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- mol
- liposome
- oligoglycerin
- 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.)
- Pending
Links
- 125000001095 phosphatidyl group Chemical group 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 239000002502 liposome Substances 0.000 claims abstract description 102
- 210000004369 blood Anatomy 0.000 claims abstract description 10
- 239000008280 blood Substances 0.000 claims abstract description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 40
- -1 alkyl phospholipids Chemical class 0.000 claims description 37
- 150000003904 phospholipids Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 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 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000002632 lipids Chemical class 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 235000011187 glycerol Nutrition 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 150000005846 sugar alcohols Chemical class 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 235000012000 cholesterol Nutrition 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 230000000865 phosphorylative effect Effects 0.000 claims description 4
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000005538 encapsulation Methods 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 description 81
- 239000000047 product Substances 0.000 description 36
- 125000006239 protecting group Chemical group 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 150000002118 epoxides Chemical class 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000013067 intermediate product Substances 0.000 description 16
- 210000000952 spleen Anatomy 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 15
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- 238000009825 accumulation Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 210000004185 liver Anatomy 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000007142 ring opening reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 230000008030 elimination Effects 0.000 description 8
- 238000003379 elimination reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000004665 fatty acids Chemical group 0.000 description 7
- 210000000056 organ Anatomy 0.000 description 7
- 238000006366 phosphorylation reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000026731 phosphorylation Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 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
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 238000005574 benzylation reaction Methods 0.000 description 4
- 230000017531 blood circulation Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000003827 glycol group Chemical group 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000006264 debenzylation reaction Methods 0.000 description 3
- 229960004679 doxorubicin Drugs 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 3
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-M [(2r)-2,3-di(hexadecanoyloxy)propyl] hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)([O-])=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229940047124 interferons Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 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 2
- 238000005866 tritylation reaction Methods 0.000 description 2
- PHJIZHSZHXTTCK-DDHJBXDOSA-N (4s,5s,6s,7s)-2,9-dimethyldeca-2,8-diene-3,4,5,6,7,8-hexol Chemical compound CC(C)=C(O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=C(C)C PHJIZHSZHXTTCK-DDHJBXDOSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- LEAQUNCACNBDEV-KHPPLWFESA-N (Z)-undec-1-en-1-ol Chemical compound CCCCCCCCC\C=C/O LEAQUNCACNBDEV-KHPPLWFESA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- JEJLGIQLPYYGEE-XIFFEERXSA-N 1,2-dipalmitoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-XIFFEERXSA-N 0.000 description 1
- CUCQUBALWPZIHL-UHFFFAOYSA-N 1-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)pentan-1-one Chemical compound O1CCOCCOCCOCCOC2=CC(C(=O)CCCC)=CC=C21 CUCQUBALWPZIHL-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- CPUUZMPWOQDKLG-NTHVSDAKSA-N C(CCCCCCCCCCCCCCCCC)C([C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O)[C@H](O)CO)O Chemical compound C(CCCCCCCCCCCCCCCCC)C([C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O)[C@H](O)CO)O CPUUZMPWOQDKLG-NTHVSDAKSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-Threitol Natural products OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
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- 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]
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- 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009223478A Division JP2009298817A (ja) | 1996-02-16 | 2009-09-28 | ホスファチジルオリゴグリセリン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000506121A true JP2000506121A (ja) | 2000-05-23 |
| JP2000506121A5 JP2000506121A5 (enExample) | 2004-11-18 |
Family
ID=26022970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9529011A Pending JP2000506121A (ja) | 1996-02-16 | 1997-02-17 | ホスファチジルオリゴグリセリン |
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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001515082A (ja) * | 1997-08-18 | 2001-09-18 | マツクス−プランク−ゲゼルシヤフト ツール フエルデルング デル ヴイツセンシヤフテン エー フアウ | リン脂質類似化合物 |
| JP2005505573A (ja) * | 2001-09-28 | 2005-02-24 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | リポソーム中の（エステル）−リゾレシチン |
| JP2016523242A (ja) * | 2013-06-18 | 2016-08-08 | 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 |
| WO2022154055A1 (ja) * | 2021-01-13 | 2022-07-21 | 地方独立行政法人神奈川県立産業技術総合研究所 | ポリグリセロール、該ポリグリセロールを含む複合ゲル組成物、該複合ゲル組成物を含む薬剤送達マイクロニードルおよびそれらの製造方法 |
Families Citing this family (18)
| 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. |
| 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 |
| 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 |
| 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 |
| 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
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001515082A (ja) * | 1997-08-18 | 2001-09-18 | マツクス−プランク−ゲゼルシヤフト ツール フエルデルング デル ヴイツセンシヤフテン エー フアウ | リン脂質類似化合物 |
| JP2010018625A (ja) * | 1997-08-18 | 2010-01-28 | Max-Planck-Ges Zur Foerderung Der Wissenschaften Ev | リン脂質類似化合物 |
| JP2005505573A (ja) * | 2001-09-28 | 2005-02-24 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | リポソーム中の（エステル）−リゾレシチン |
| JP2016523242A (ja) * | 2013-06-18 | 2016-08-08 | 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 |
| US10251838B2 (en) | 2013-06-18 | 2019-04-09 | THERMOSOME GmbH | Stereospecific lipids for locoregional therapy with long-term circulating stimuli-sensitive nanocarrier systems |
| WO2022154055A1 (ja) * | 2021-01-13 | 2022-07-21 | 地方独立行政法人神奈川県立産業技術総合研究所 | ポリグリセロール、該ポリグリセロールを含む複合ゲル組成物、該複合ゲル組成物を含む薬剤送達マイクロニードルおよびそれらの製造方法 |
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 |
| WO1997030058A1 (de) | 1997-08-21 |
| AU1791297A (en) | 1997-09-02 |
| CA2246568C (en) | 2007-08-07 |
| US20030053978A1 (en) | 2003-03-20 |
| ATE244254T1 (de) | 2003-07-15 |
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