CA2763819A1 - Pure peg-lipid conjugates - Google Patents
Pure peg-lipid conjugates Download PDFInfo
- Publication number
- CA2763819A1 CA2763819A1 CA2763819A CA2763819A CA2763819A1 CA 2763819 A1 CA2763819 A1 CA 2763819A1 CA 2763819 A CA2763819 A CA 2763819A CA 2763819 A CA2763819 A CA 2763819A CA 2763819 A1 CA2763819 A1 CA 2763819A1
- Authority
- CA
- Canada
- Prior art keywords
- peg
- glycerol
- lipid
- acid
- glycol
- 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.)
- Abandoned
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 152
- 150000002632 lipids Chemical class 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims description 91
- 239000000126 substance Substances 0.000 claims description 59
- 125000005647 linker group Chemical group 0.000 claims description 46
- 239000003613 bile acid Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 21
- 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 18
- 235000012000 cholesterol Nutrition 0.000 claims description 9
- 125000003473 lipid group Chemical group 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 abstract description 183
- 239000002202 Polyethylene glycol Substances 0.000 abstract description 156
- 238000003786 synthesis reaction Methods 0.000 abstract description 36
- 230000015572 biosynthetic process Effects 0.000 abstract description 31
- 229920000642 polymer Polymers 0.000 abstract description 15
- 230000008901 benefit Effects 0.000 abstract description 7
- 238000001308 synthesis method Methods 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 48
- 239000003814 drug Substances 0.000 description 48
- 229940079593 drug Drugs 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000243 solution Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 33
- 235000011187 glycerol Nutrition 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002156 mixing Methods 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- 125000006239 protecting group Chemical group 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- -1 polyethylene Polymers 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000013543 active substance Substances 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 19
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 150000002314 glycerols Chemical group 0.000 description 15
- 150000003573 thiols Chemical class 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000008186 active pharmaceutical agent Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 229940088679 drug related substance Drugs 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229960004130 itraconazole Drugs 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 9
- 239000008213 purified water Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002246 antineoplastic agent Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 7
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229930182912 cyclosporin Natural products 0.000 description 6
- 238000012377 drug delivery Methods 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 5
- OWVYGSGZMWWQQY-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]-1-methoxyethanol Chemical compound COC(O)COCCOCCOCCOCCOCCO OWVYGSGZMWWQQY-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- 239000004698 Polyethylene Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 238000006266 etherification reaction Methods 0.000 description 5
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 5
- 229920001427 mPEG Polymers 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229940068917 polyethylene glycols Drugs 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 5
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 4
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005587 carbonate group Chemical group 0.000 description 4
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- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
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- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6905—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
- A61K47/6911—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Landscapes
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- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Polyethers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US21762709P | 2009-06-02 | 2009-06-02 | |
| US61/217,627 | 2009-06-02 | ||
| US28406509P | 2009-12-12 | 2009-12-12 | |
| US61/284,065 | 2009-12-12 | ||
| PCT/US2010/001590 WO2010141069A2 (en) | 2009-06-02 | 2010-06-01 | Pure peg-lipid conjugates |
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| CA2763819A1 true CA2763819A1 (en) | 2010-12-09 |
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| CA2763819A Abandoned CA2763819A1 (en) | 2009-06-02 | 2010-06-01 | Pure peg-lipid conjugates |
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| US20120202890A1 (en) * | 2011-02-08 | 2012-08-09 | Nian Wu | Polymer-carbohydrate-lipid conjugates |
| WO2012122144A1 (en) * | 2011-03-07 | 2012-09-13 | Wu Nian | Highly monodisperse branched peg-lipid conjugates |
| US10196637B2 (en) | 2011-06-08 | 2019-02-05 | Nitto Denko Corporation | Retinoid-lipid drug carrier |
| US8883177B2 (en) | 2011-06-28 | 2014-11-11 | Nian Wu | Pharmaceutical compositions for parenteral administration |
| JP6051758B2 (ja) * | 2011-10-17 | 2016-12-27 | 日油株式会社 | ジアシルグリセロールと結合した分岐型ポリエチレングリコール、その製造方法およびポリエチレングリコール修飾リポソーム |
| BR112015003658B1 (pt) * | 2012-08-21 | 2022-09-27 | Opko Pharmaceuticals, Llc | Formulação oftálmica, uso da dita formulação no tratamento de doença oftálmica do segmento posterior, formulação de lipossomas e suspensão oftálmica lipossomal |
| US11458199B2 (en) | 2012-08-21 | 2022-10-04 | Opko Pharmaceuticals, Llc | Liposome formulations |
| PL2887923T3 (pl) | 2012-08-24 | 2023-08-14 | Sun Pharmaceutical Industries Limited | Preparat okulistyczny polioksylipidu lub polioksylowego kwasu tłuszczowego i leczenie chorób oczu |
| WO2015021044A1 (en) * | 2013-08-05 | 2015-02-12 | University Of Rochester | Compositions and methods for stimuli-responsive release of a therapeutic agent |
| CA2932123C (en) * | 2013-12-05 | 2022-05-31 | Nian WU | Polymer-carbohydrate conjugates for drug delivery technology |
| CA2930505C (en) * | 2013-12-20 | 2019-06-18 | F. Hoffman-La Roche Ag | Compounds comprising one or more hydrophobic domains and a hydrophilic domain comprising peg moieties, useful for binding cells |
| CN105829886B (zh) | 2013-12-20 | 2018-04-03 | 豪夫迈·罗氏有限公司 | 使用包含聚乙二醇部分的化合物在支持物上固定细胞的方法 |
| JP6461973B2 (ja) * | 2013-12-20 | 2019-01-30 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ２以上の疎水性ドメインおよびｐｅｇ部分を含む親水性ドメインを含む化合物の、細胞の安定化のための使用 |
| AU2015360794B2 (en) | 2014-12-08 | 2021-07-08 | The Board Of Regents Of The University Of Texas System | Lipocationic polymers and uses thereof |
| US10064954B2 (en) * | 2015-06-23 | 2018-09-04 | Nian Wu | Polymer-cyclodextrin-lipid conjugates |
| KR102764250B1 (ko) | 2015-09-14 | 2025-02-07 | 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 | 지질양이온성 덴드리머 및 이의 용도 |
| DK3373976T3 (da) | 2015-11-10 | 2024-04-02 | Sun Pharmaceutical Ind Ltd | Topiske formuleringer og anvendelser deraf |
| DK3386484T3 (da) | 2015-12-10 | 2022-07-04 | Modernatx Inc | Sammensætninger og fremgangsmåder til afgivelse af terapeutiske midler |
| CN106905120B (zh) * | 2015-12-21 | 2020-04-28 | 北京键凯科技股份有限公司 | Y型多缩乙二醇衍生物及其制备方法 |
| NZ785158A (en) | 2016-02-29 | 2025-03-28 | Sun Pharmaceutical Ind Ltd | Topical cyclosporine-containing formulations and uses thereof |
| PL3458074T3 (pl) | 2016-05-16 | 2024-11-12 | Board Of Regents Of The University Of Texas System | KOMPOZYCJA DO DOSTARCZANIA tRNA W POSTACI NANOCZĄSTEK I SPOSOBY ICH STOSOWANIA |
| CN114656378A (zh) | 2016-05-16 | 2022-06-24 | 得克萨斯州大学系统董事会 | 阳离子磺酰胺氨基脂质和两亲性两性离子氨基脂质 |
| WO2018170270A1 (en) | 2017-03-15 | 2018-09-20 | Modernatx, Inc. | Varicella zoster virus (vzv) vaccine |
| CA3094055A1 (en) * | 2018-03-20 | 2019-09-26 | Nof Corporation | Branched monodispersed polyethylene glycol, intermediate and methods for producing same |
| WO2019189188A1 (ja) * | 2018-03-29 | 2019-10-03 | 日油株式会社 | トリチル基含有単分散ポリエチレングリコールの精製方法 |
| WO2019191597A1 (en) * | 2018-03-30 | 2019-10-03 | The Board Of Regents Of The University Of Oklahoma | Very long chain saturated fatty acid compounds, compositions containing same, and methods of use |
| US12357580B2 (en) | 2018-06-19 | 2025-07-15 | The Board Of Regents Of The University Of Texas System | Lipid nanoparticle compositions for delivery of mRNA and long nucleic acids |
| GB2600800B (en) | 2018-09-04 | 2023-08-16 | Univ Texas | Compositions and methods for organ specific delivery of nucleic acids |
| GB2606038B (en) | 2018-09-04 | 2023-05-03 | Univ Texas | Compositions and methods for organ specific delivery of nucleic acids |
| CN112996854B (zh) * | 2018-09-19 | 2024-08-30 | 摩登纳特斯有限公司 | 高纯度peg脂质和其用途 |
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|---|---|---|---|---|
| US5827533A (en) * | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
| US7141552B2 (en) * | 2000-01-10 | 2006-11-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Use of lipid conjugates in the treatment of diseases |
| CN1882693B (zh) * | 2003-09-15 | 2012-08-15 | 普洛体维生物治疗公司 | 聚乙二醇修饰的脂质化合物及其应用 |
| WO2006007712A1 (en) * | 2004-07-19 | 2006-01-26 | Protiva Biotherapeutics, Inc. | Methods comprising polyethylene glycol-lipid conjugates for delivery of therapeutic agents |
| WO2006051405A2 (en) * | 2004-11-12 | 2006-05-18 | Cambridge University Technical Services Ltd. | Methods and means related to cancer stem cells |
| CA2705797A1 (en) * | 2007-11-14 | 2009-05-22 | The Regents Of The University Of California | Sterol-modified amphiphilic lipids |
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- 2010-06-01 WO PCT/US2010/001590 patent/WO2010141069A2/en not_active Ceased
- 2010-06-01 KR KR1020117031713A patent/KR20120039564A/ko not_active Withdrawn
- 2010-06-01 EP EP10783699A patent/EP2437756A2/en not_active Withdrawn
- 2010-06-01 US US12/802,197 patent/US20110040113A1/en not_active Abandoned
- 2010-06-01 AP AP2012006053A patent/AP2012006053A0/xx unknown
- 2010-06-01 JP JP2012513928A patent/JP2012528857A/ja active Pending
- 2010-06-01 AU AU2010257181A patent/AU2010257181A1/en not_active Abandoned
- 2010-06-01 CN CN2010800303714A patent/CN102665685A/zh active Pending
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| BRPI1010175A2 (pt) | 2016-03-29 |
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| JP2012528857A (ja) | 2012-11-15 |
| US20110040113A1 (en) | 2011-02-17 |
| ZA201109366B (en) | 2012-08-29 |
| WO2010141069A3 (en) | 2012-04-12 |
| IL216719A0 (en) | 2012-02-29 |
| CL2011003049A1 (es) | 2012-07-13 |
| MX2011012823A (es) | 2012-06-25 |
| CN102665685A (zh) | 2012-09-12 |
| AU2010257181A1 (en) | 2012-01-12 |
| WO2010141069A2 (en) | 2010-12-09 |
| CO6511284A2 (es) | 2012-08-31 |
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