JP2004528321A5 - - Google Patents
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- Publication number
- JP2004528321A5 JP2004528321A5 JP2002579019A JP2002579019A JP2004528321A5 JP 2004528321 A5 JP2004528321 A5 JP 2004528321A5 JP 2002579019 A JP2002579019 A JP 2002579019A JP 2002579019 A JP2002579019 A JP 2002579019A JP 2004528321 A5 JP2004528321 A5 JP 2004528321A5
- Authority
- JP
- Japan
- Prior art keywords
- complex
- saponin
- sterol
- primary
- group
- 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.)
- Withdrawn
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- 150000007949 saponins Chemical group 0.000 claims 36
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims 33
- 229930182490 saponin Natural products 0.000 claims 33
- 229930182558 Sterol Natural products 0.000 claims 29
- 150000003432 sterols Chemical group 0.000 claims 29
- 235000003702 sterols Nutrition 0.000 claims 29
- 230000002163 immunogen Effects 0.000 claims 14
- 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 8
- 239000000203 mixture Substances 0.000 claims 8
- 230000000890 antigenic effect Effects 0.000 claims 7
- 241001465754 Metazoa Species 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229920001184 polypeptide Polymers 0.000 claims 6
- 102000004196 processed proteins & peptides Human genes 0.000 claims 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims 6
- 239000002131 composite material Substances 0.000 claims 5
- 102000039446 nucleic acids Human genes 0.000 claims 5
- 108020004707 nucleic acids Proteins 0.000 claims 5
- 150000007523 nucleic acids Chemical class 0.000 claims 5
- 235000009001 Quillaja saponaria Nutrition 0.000 claims 4
- 235000012000 cholesterol Nutrition 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 241001454523 Quillaja saponaria Species 0.000 claims 3
- 235000014633 carbohydrates Nutrition 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000002405 diagnostic procedure Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000002209 hydrophobic effect Effects 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- -1 mycostol Chemical compound 0.000 claims 3
- 150000003904 phospholipids Chemical class 0.000 claims 3
- 102000040430 polynucleotide Human genes 0.000 claims 3
- 108091033319 polynucleotide Proteins 0.000 claims 3
- 239000002157 polynucleotide Substances 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims 2
- 150000001720 carbohydrates Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 2
- 239000000344 soap Substances 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims 1
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims 1
- QGVQZRDQPDLHHV-DPAQBDIFSA-N (3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3-thiol Chemical compound C1C=C2C[C@@H](S)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 QGVQZRDQPDLHHV-DPAQBDIFSA-N 0.000 claims 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims 1
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 claims 1
- 108010001857 Cell Surface Receptors Proteins 0.000 claims 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 claims 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 claims 1
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 claims 1
- 241001092142 Molina Species 0.000 claims 1
- 241001644525 Nastus productus Species 0.000 claims 1
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims 1
- 241001092473 Quillaja Species 0.000 claims 1
- 108010084592 Saporins Proteins 0.000 claims 1
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims 1
- ISXSJGHXHUZXNF-LXZPIJOJSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] n-[2-(dimethylamino)ethyl]carbamate;hydrochloride Chemical compound Cl.C1C=C2C[C@@H](OC(=O)NCCN(C)C)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 ISXSJGHXHUZXNF-LXZPIJOJSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims 1
- 239000012867 bioactive agent Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 claims 1
- 229940058690 lanosterol Drugs 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- DNVPQKQSNYMLRS-YAPGYIAOSA-N lumisterol Chemical compound C1[C@@H](O)CC[C@@]2(C)[C@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-YAPGYIAOSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 102000006240 membrane receptors Human genes 0.000 claims 1
- 239000011859 microparticle Substances 0.000 claims 1
- 239000004005 microsphere Substances 0.000 claims 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 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 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims 1
- 235000015500 sitosterol Nutrition 0.000 claims 1
- 229950005143 sitosterol Drugs 0.000 claims 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229930003352 steroid alkaloid Natural products 0.000 claims 1
- 229930002534 steroid glycoside Natural products 0.000 claims 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims 1
- 235000016831 stigmasterol Nutrition 0.000 claims 1
- 229940032091 stigmasterol Drugs 0.000 claims 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200100560 | 2001-04-04 | ||
| US30860901P | 2001-07-31 | 2001-07-31 | |
| PCT/DK2002/000229 WO2002080981A2 (en) | 2001-04-04 | 2002-04-04 | Polynucleotide binding complexes comprising sterols and saponins |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010120290A Division JP2010180249A (ja) | 2001-04-04 | 2010-05-26 | ステロールおよびサポニンを含むポリヌクレオチド結合複合体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004528321A JP2004528321A (ja) | 2004-09-16 |
| JP2004528321A5 true JP2004528321A5 (https=) | 2005-12-22 |
Family
ID=26069002
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002579019A Withdrawn JP2004528321A (ja) | 2001-04-04 | 2002-04-04 | ステロールおよびサポニンを含むポリヌクレオチド結合複合体 |
| JP2010120290A Pending JP2010180249A (ja) | 2001-04-04 | 2010-05-26 | ステロールおよびサポニンを含むポリヌクレオチド結合複合体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010120290A Pending JP2010180249A (ja) | 2001-04-04 | 2010-05-26 | ステロールおよびサポニンを含むポリヌクレオチド結合複合体 |
Country Status (7)
| Country | Link |
|---|---|
| EP (2) | EP1377320B1 (https=) |
| JP (2) | JP2004528321A (https=) |
| AT (1) | ATE409495T1 (https=) |
| DE (1) | DE60229118D1 (https=) |
| DK (1) | DK1377320T3 (https=) |
| NZ (1) | NZ529347A (https=) |
| WO (1) | WO2002080981A2 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE449612T1 (de) * | 2002-10-02 | 2009-12-15 | Nordic Vaccine Technology As | Zusammensetzung zur impfung |
| WO2009106085A1 (en) * | 2008-02-28 | 2009-09-03 | Nordic Vaccine A/S | Vaccine compositions comprising saccharide antigens |
| DK2750683T4 (da) * | 2011-10-03 | 2021-04-12 | Croda Int Plc | Nanopartikler, fremgangsmåde til fremstilling og anvendelse deraf som bærer for amfipatiske eller hydrofobe molekyler inden for medicin, herunder cancerbehandling, og i fødevarerelaterede forbindelser |
| AR095962A1 (es) | 2013-04-01 | 2015-11-25 | Moreinx Ab | Nanopartículas, compuestas de esterol y saponina de quillaja saponaria molina, proceso para preparación y uso de las mismas como portadores para moléculas anfipáticas o hidrófobas en el campo de la medicina incluyendo tratamiento de cáncer y compuestos relacionados con alimentos |
| US11708388B2 (en) | 2017-07-11 | 2023-07-25 | Freie Universität Berlin | Uses of a saponin and method for its isolation |
| CN108498376B (zh) * | 2018-04-02 | 2020-11-13 | 榛硕（武汉）智能科技有限公司 | 一种甲基硅油乳液及其制备方法 |
| CN109295080B (zh) * | 2018-09-19 | 2021-08-20 | 昆明理工大学 | 珠子参β-香树脂醇合成酶基因Pjβ-AS的用途 |
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| US5273965A (en) | 1992-07-02 | 1993-12-28 | Cambridge Biotech Corporation | Methods for enhancing drug delivery with modified saponins |
| US5650398A (en) | 1992-07-02 | 1997-07-22 | Cambridge Biotech Corporation | Drug delivery enhancement via modified saponins |
| AU1077795A (en) | 1993-09-30 | 1995-04-18 | Seed Capital Investments (Sci) B.V. | Compounds with adjuvant activity |
| AU2112697A (en) * | 1996-02-09 | 1997-08-28 | Pi-Wan Cheng | Receptor ligand-facilitated delivery of biologically active molecules |
| NZ333562A (en) | 1996-06-25 | 2001-04-27 | Stichting Inst Voor Dierhouder | Vaccine comprising antigens bound by thioester or disulphide bonds to fatty acid carriers such palmitic acid, antigens bound in reversible and labile way |
| JP3963506B2 (ja) * | 1996-08-26 | 2007-08-22 | 俊彦 松尾 | リポソーム点眼剤 |
| AUPO517897A0 (en) * | 1997-02-19 | 1997-04-11 | Csl Limited | Chelating immunostimulating complexes |
| US6120751A (en) | 1997-03-21 | 2000-09-19 | Imarx Pharmaceutical Corp. | Charged lipids and uses for the same |
| CA2287976A1 (fr) * | 1997-04-30 | 1998-11-05 | Bruno Guy | Composition vaccinale anti-helicobacter comprenant un adjuvant de type th1 |
| US6080725A (en) | 1997-05-20 | 2000-06-27 | Galenica Pharmaceuticals, Inc. | Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof |
| AUPO732997A0 (en) * | 1997-06-12 | 1997-07-03 | Csl Limited | Ganglioside immunostimulating complexes and uses thereof |
| DE19740092A1 (de) * | 1997-09-12 | 1999-03-18 | Ulrich Dr Med Hengge | Liposomen und Verfahren zur Transfektion von Zellen |
| US6013258A (en) * | 1997-10-09 | 2000-01-11 | Zycos Inc. | Immunogenic peptides from the HPV E7 protein |
| EP1156783B1 (en) * | 1999-03-02 | 2007-10-24 | Transave, Inc. | Encapsulation of bioactive complexes in liposomes |
| AU2001246393A1 (en) | 2000-03-31 | 2001-10-08 | Vaccine Chip Technology Aps | Immunostimulating properties of a fragment of tgf-beta |
-
2002
- 2002-04-04 WO PCT/DK2002/000229 patent/WO2002080981A2/en not_active Ceased
- 2002-04-04 EP EP02759762A patent/EP1377320B1/en not_active Expired - Lifetime
- 2002-04-04 DE DE60229118T patent/DE60229118D1/de not_active Expired - Lifetime
- 2002-04-04 AT AT02759762T patent/ATE409495T1/de not_active IP Right Cessation
- 2002-04-04 EP EP08159646A patent/EP2011517A1/en not_active Withdrawn
- 2002-04-04 NZ NZ529347A patent/NZ529347A/en unknown
- 2002-04-04 JP JP2002579019A patent/JP2004528321A/ja not_active Withdrawn
- 2002-04-04 DK DK02759762T patent/DK1377320T3/da active
-
2010
- 2010-05-26 JP JP2010120290A patent/JP2010180249A/ja active Pending
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