AU707779C - Substituted liposaccharides useful in the treatment and prevention of endotoxemia - Google Patents
Substituted liposaccharides useful in the treatment and prevention of endotoxemiaInfo
- Publication number
- AU707779C AU707779C AU63802/96A AU6380296A AU707779C AU 707779 C AU707779 C AU 707779C AU 63802/96 A AU63802/96 A AU 63802/96A AU 6380296 A AU6380296 A AU 6380296A AU 707779 C AU707779 C AU 707779C
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- branched
- straight
- compound
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 208000037487 Endotoxemia Diseases 0.000 title abstract description 12
- 230000002265 prevention Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000006539 C12 alkyl group Chemical group [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])* 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000002704 decyl group Chemical group [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])* 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 abstract description 89
- 238000000034 method Methods 0.000 abstract description 17
- 206010040070 Septic Shock Diseases 0.000 abstract description 10
- 230000036303 septic shock Effects 0.000 abstract description 9
- 206010040047 Sepsis Diseases 0.000 abstract description 8
- 230000000069 prophylactic effect Effects 0.000 abstract description 6
- 208000013223 septicemia Diseases 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
- 239000000203 mixture Substances 0.000 description 117
- 239000000243 solution Substances 0.000 description 103
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
- 239000002158 endotoxin Substances 0.000 description 60
- 239000002904 solvent Substances 0.000 description 49
- 230000002829 reductive effect Effects 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 229920006008 lipopolysaccharide Polymers 0.000 description 41
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 239000000377 silicon dioxide Substances 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- 239000011734 sodium Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 27
- 229910052708 sodium Inorganic materials 0.000 description 27
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- 235000000346 sugar Nutrition 0.000 description 19
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
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- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 239000006188 syrup Substances 0.000 description 17
- 235000020357 syrup Nutrition 0.000 description 17
- 102000003390 tumor necrosis factor Human genes 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
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- 230000005764 inhibitory process Effects 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- -1 disaccharide compounds Chemical class 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
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- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
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Landscapes
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- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
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- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Otolaryngology (AREA)
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- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/461,675 US5750664A (en) | 1995-06-05 | 1995-06-05 | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
| US08/461675 | 1995-06-05 | ||
| PCT/US1996/009578 WO1996039411A1 (en) | 1995-06-05 | 1996-06-05 | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
Publications (3)
| Publication Number | Publication Date |
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| AU6380296A AU6380296A (en) | 1996-12-24 |
| AU707779B2 AU707779B2 (en) | 1999-07-22 |
| AU707779C true AU707779C (en) | 2001-12-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU63802/96A Expired AU707779C (en) | 1995-06-05 | 1996-06-05 | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
Country Status (21)
| Country | Link |
|---|---|
| US (8) | US5681824A (OSRAM) |
| EP (1) | EP0853627B1 (OSRAM) |
| JP (3) | JP4009318B2 (OSRAM) |
| KR (1) | KR100416335B1 (OSRAM) |
| CN (1) | CN1067082C (OSRAM) |
| AT (1) | ATE258185T1 (OSRAM) |
| AU (1) | AU707779C (OSRAM) |
| CA (1) | CA2223140C (OSRAM) |
| DE (1) | DE69631376T2 (OSRAM) |
| DK (1) | DK0853627T3 (OSRAM) |
| ES (1) | ES2214543T3 (OSRAM) |
| HU (1) | HU221342B1 (OSRAM) |
| IL (2) | IL122251A0 (OSRAM) |
| MX (1) | MX9709502A (OSRAM) |
| NO (1) | NO310239B1 (OSRAM) |
| NZ (1) | NZ312299A (OSRAM) |
| PT (1) | PT853627E (OSRAM) |
| RU (1) | RU2170738C2 (OSRAM) |
| TW (1) | TW366345B (OSRAM) |
| WO (1) | WO1996039411A1 (OSRAM) |
| ZA (1) | ZA964666B (OSRAM) |
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| US5681824A (en) * | 1995-06-05 | 1997-10-28 | Eisai Co., Ltd. | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
| US6417172B1 (en) * | 1995-06-05 | 2002-07-09 | Eisai Co., Ltd. | Prevention and treatment of pulmonary bacterial infection or symptomatic pulmonary exposure to endotoxin by inhalation of antiendotoxin drugs |
| ES2242226T3 (es) * | 1996-07-03 | 2005-11-01 | Eisai Co., Ltd. | Composiciones que contienen analogos del lipido a y procedimiento parasu preparacion. |
| WO2000013029A1 (en) * | 1998-09-01 | 2000-03-09 | Eisai Co., Ltd | Method for evaluating lipid a analog-containing injections |
| US20030130212A1 (en) * | 1999-01-14 | 2003-07-10 | Rossignol Daniel P. | Administration of an anti-endotoxin drug by intravenous infusion |
| EP1158990B1 (en) * | 1999-01-14 | 2007-10-17 | Eisai R&D Management Co., Ltd. | Use of e5564 for the treatment of sepsis by intravenous infusion |
| US6835721B2 (en) | 1999-02-01 | 2004-12-28 | Eisai Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| US20040006242A1 (en) * | 1999-02-01 | 2004-01-08 | Hawkins Lynn D. | Immunomodulatory compounds and method of use thereof |
| US7915238B2 (en) * | 1999-02-01 | 2011-03-29 | Eisai R & D Management Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| HK1040519A1 (en) * | 1999-02-10 | 2002-06-14 | Sankyo Company, Limited | Ether type lipid a1-carboxylic acid analogues |
| US20050101549A1 (en) * | 2000-01-14 | 2005-05-12 | Melvyn Lynn | Prevention and treatment of endotoxemia and related complications associated with surgery |
| AU2001229479A1 (en) * | 2000-01-14 | 2001-07-24 | Eisai Co. Ltd. | Prevention and treatment of endotoxemia and related complications associated with surgery |
| AU3850701A (en) | 2000-02-18 | 2001-08-27 | Eisai Co Ltd | Micelles |
| US6861512B2 (en) | 2000-03-01 | 2005-03-01 | Eisai Co., Ltd. | Separation of olefinic isomers |
| US20030105033A1 (en) * | 2000-06-09 | 2003-06-05 | Rossignol Daniel P. | Administration of an anti-endotoxin drug by bolus or intermittent intravenous infusion |
| EP1363642A4 (en) * | 2000-06-09 | 2005-02-02 | Eisai Co Ltd | ADMINISTRATION OF ANTI-ENDOTOXIN DRUG BY INJECTION OF A BOWL OR BY INTERMITTENT INTRAVENOUS INFUSION |
| WO2002088072A1 (en) * | 2001-04-23 | 2002-11-07 | Eisai Co., Ltd. | Process for preparation of alkylene compounds |
| WO2002088062A1 (en) * | 2001-04-23 | 2002-11-07 | Eisai Co., Ltd. | Process for preparation of alcohol derivatives |
| WO2002085117A1 (en) * | 2001-04-24 | 2002-10-31 | Eisai Co., Ltd. | Methods and compositions for preventing and treating septic shock and endotoxemia |
| JP4366081B2 (ja) * | 2001-05-22 | 2009-11-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 高度に精製されたアンチエンドトキシン化合物 |
| DE10125179A1 (de) * | 2001-05-23 | 2002-12-05 | Laves Ralph Georg | Verwendung von LPS zur Behandlung intestinaler Entzündungsprozesse |
| AU2002323106A1 (en) * | 2001-08-10 | 2003-02-24 | Eisai Co., Ltd. | Treatment and prevention of heat shock protein-associated diseases and conditions |
| US7727974B2 (en) * | 2001-08-10 | 2010-06-01 | Eisai R & D Management Co., Ltd. | Methods of reducing the severity of mucositis |
| WO2003050137A2 (en) * | 2001-12-11 | 2003-06-19 | David Schwartz | Toll-like receptor 4 mutations |
| AU2002950657A0 (en) * | 2002-08-08 | 2002-09-12 | Alchemia Limited | Derivatives of monosaccharides for drug discovery |
| AU2002951995A0 (en) * | 2002-10-11 | 2002-10-31 | Alchemia Limited | Classes of compounds that interact with gpcrs |
| AU2003289493A1 (en) * | 2002-12-24 | 2004-07-22 | Mochizuki, Takashi | Lipid a analogues having glucose as the right sugar |
| PT1589934E (pt) * | 2003-01-06 | 2016-01-26 | Corixa Corp | Determinados compostos de fosfato de aminoalquil glucosaminida e seu uso |
| EP1587830B1 (en) * | 2003-01-28 | 2009-07-08 | Academisch Ziekenhuis Leiden | Peptide inhibitors of toxins derived from ll-37 |
| US7906633B2 (en) * | 2003-02-20 | 2011-03-15 | Eisai R&D Management Co., Ltd. | Reagents and methods for preparing LPS antagonist B1287 and stereoisomers thereof |
| RU2005130771A (ru) * | 2003-03-05 | 2006-01-27 | Эйсай Ко., Лтд. (JP) | Композиции и способы профилактики и лечения эндотоксин-связанных заболеваний и состояний |
| WO2005027826A2 (en) * | 2003-07-14 | 2005-03-31 | Eisai, Co, Ltd. | Methods and treating severe acute respiratory syndrome |
| WO2005059517A2 (en) | 2003-12-16 | 2005-06-30 | University Of Massachusetts | Toll-like receptor assays |
| WO2005066193A1 (ja) * | 2004-01-08 | 2005-07-21 | Sankyo Company, Limited | 左糖グルコースリピドa類縁体 |
| US20070292418A1 (en) * | 2005-04-26 | 2007-12-20 | Eisai Co., Ltd. | Compositions and methods for immunotherapy |
| CN103285392A (zh) | 2005-04-26 | 2013-09-11 | 卫材R&D管理株式会社 | 用于癌症免疫疗法的组合物和其用途 |
| US20100015125A1 (en) * | 2005-06-17 | 2010-01-21 | University Of Rochester | Methods and compositions for enhancing immune memory by blocking intrahepatic activated t cell deletion |
| JP5118968B2 (ja) * | 2005-08-31 | 2013-01-16 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | リピッドａ類縁体の製造方法 |
| WO2007026675A1 (ja) * | 2005-08-31 | 2007-03-08 | Eisai R & D Management Co., Ltd. | リピッドａ類縁体の製造方法 |
| US7943588B2 (en) | 2006-03-28 | 2011-05-17 | Trustees Of Dartmouth College | Method for preventing or treating neuropathic pain |
| WO2008059307A2 (en) * | 2006-11-16 | 2008-05-22 | Om Pharma | Functionalized beta 1,6 glucosamine disaccharides and process for their preparation |
| WO2008062842A1 (fr) | 2006-11-22 | 2008-05-29 | Eisai R & D Management Co., Ltd. | Sel de sodium de disaccharide et ses méthodes de production et d'utilisation |
| JP5244608B2 (ja) * | 2006-11-22 | 2013-07-24 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 二糖類化合物のナトリウム塩及びその製造方法並びにその使用 |
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| WO2011038537A1 (zh) * | 2009-09-29 | 2011-04-07 | 上海南方基因科技有限公司 | 败血症以及败血症休克的预测、预防和治疗方法及试剂盒 |
| GB201013785D0 (en) | 2010-08-17 | 2010-09-29 | Ucl Business Plc | Treatment |
| JP2012246470A (ja) | 2011-05-31 | 2012-12-13 | Sharp Corp | 半導体ナノ粒子の製造方法、半導体ナノ粒子、ならびにこれを用いた蛍光体 |
| HK1203474A1 (en) * | 2011-12-22 | 2015-10-30 | Nanoco Technologies Limited | Surface modified nanoparticles |
| BR112014024139A8 (pt) | 2012-03-28 | 2018-01-16 | Univ Maryland | administração de eritoran ou sais farmaceuticamente aceitáveis do mesmo para tratar infecções de ortomixovírus |
| WO2014113048A1 (en) * | 2013-01-18 | 2014-07-24 | Loma Linda University | Compositions and methods for diagnosing and treating sepsis |
| WO2015006740A2 (en) | 2013-07-11 | 2015-01-15 | Alnylam Pharmaceuticals, Inc. | Oligonucleotide-ligand conjugates and process for their preparation |
| US9584991B1 (en) * | 2014-06-19 | 2017-02-28 | Isaac S. Daniel | Method of communicating and accessing social networks using interactive coded messages |
| EP3436467B1 (en) * | 2016-03-30 | 2025-08-06 | Ayuvis Research, Inc. | Beta-anomer-saccharides for use in the treatment of sepsis, septic shock, septicemia, burn or wound infection |
| US10570074B2 (en) | 2016-09-14 | 2020-02-25 | Genomatica, Inc. | 1,3-fatty diol compounds and derivatives thereof |
| EP3512508B1 (en) * | 2016-09-16 | 2022-03-16 | Eisai R&D Management Co., Ltd. | Method of use of eritoran as a tlr4 antagonist for treatment of ebola and marburg disease |
| BR112021010717A2 (pt) * | 2018-12-17 | 2021-08-31 | Eisai R&D Management Co., Ltd. | Formulação que compreende lipossomas |
| WO2021207218A1 (en) | 2020-04-06 | 2021-10-14 | Eisai R&D Management Co., Ltd. | Treatment of nidovirales infection with eritoran |
| CN113527396B (zh) * | 2020-04-17 | 2024-02-02 | 上海医药工业研究院 | 一种疫苗佐剂mpla的中间体、合成及应用 |
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| US4495346A (en) * | 1981-03-30 | 1985-01-22 | Wisconsin Alumni Research Foundation | Method of preparing a disaccharide |
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| HU199494B (en) * | 1985-06-28 | 1990-02-28 | Sandoz Ag | Process for producing new saccharides and pharmaceutical compositions comprising same |
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| US5158939A (en) * | 1989-07-21 | 1992-10-27 | Wisconsin Alumni Research Foundation | Method of stimulating the immune systems of animals and compositions useful therefor |
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| JP3040847B2 (ja) | 1990-06-22 | 2000-05-15 | 三共株式会社 | リピドｘ類縁体 |
| AU660325B2 (en) * | 1991-10-11 | 1995-06-22 | Eisai Co. Ltd. | Anti-endotoxin compounds and related molecules and methods |
| US5530113A (en) * | 1991-10-11 | 1996-06-25 | Eisai Co., Ltd. | Anti-endotoxin compounds |
| JP3135990B2 (ja) | 1992-07-31 | 2001-02-19 | 沖電気工業株式会社 | パリティ付加回路 |
| US5413785A (en) * | 1993-01-27 | 1995-05-09 | New England Deaconess Hospital Corp. | Methodology employing lactobacillus GG for reduction of plasma endotoxin levels circulating in-vivo |
| CN1055093C (zh) * | 1993-11-17 | 2000-08-02 | 实验室奥姆公司 | 葡糖胺二糖类、其制备方法和用途、以及含有这些二糖的药物组合物 |
| US5681824A (en) * | 1995-06-05 | 1997-10-28 | Eisai Co., Ltd. | Substituted liposaccharides useful in the treatment and prevention of endotoxemia |
| US6417172B1 (en) * | 1995-06-05 | 2002-07-09 | Eisai Co., Ltd. | Prevention and treatment of pulmonary bacterial infection or symptomatic pulmonary exposure to endotoxin by inhalation of antiendotoxin drugs |
| JP4235193B2 (ja) | 2005-06-07 | 2009-03-11 | 日本電信電話株式会社 | イベント履歴蓄積装置、イベント情報検証装置、イベント履歴蓄積方法、イベント情報検証方法およびイベント情報処理システム |
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1995
- 1995-06-05 US US08/461,677 patent/US5681824A/en not_active Expired - Lifetime
- 1995-06-05 US US08/461,675 patent/US5750664A/en not_active Expired - Lifetime
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1996
- 1996-06-05 IL IL12225196A patent/IL122251A0/xx not_active IP Right Cessation
- 1996-06-05 KR KR1019970708583A patent/KR100416335B1/ko not_active Expired - Lifetime
- 1996-06-05 JP JP50186897A patent/JP4009318B2/ja not_active Expired - Lifetime
- 1996-06-05 AT AT96923234T patent/ATE258185T1/de active
- 1996-06-05 AU AU63802/96A patent/AU707779C/en not_active Expired
- 1996-06-05 DK DK96923234T patent/DK0853627T3/da active
- 1996-06-05 NZ NZ312299A patent/NZ312299A/xx not_active IP Right Cessation
- 1996-06-05 EP EP96923234A patent/EP0853627B1/en not_active Expired - Lifetime
- 1996-06-05 US US08/658,656 patent/US5935938A/en not_active Expired - Lifetime
- 1996-06-05 DE DE69631376T patent/DE69631376T2/de not_active Expired - Lifetime
- 1996-06-05 CA CA002223140A patent/CA2223140C/en not_active Expired - Lifetime
- 1996-06-05 ES ES96923234T patent/ES2214543T3/es not_active Expired - Lifetime
- 1996-06-05 ZA ZA964666A patent/ZA964666B/xx unknown
- 1996-06-05 PT PT96923234T patent/PT853627E/pt unknown
- 1996-06-05 RU RU98100107/04A patent/RU2170738C2/ru active
- 1996-06-05 WO PCT/US1996/009578 patent/WO1996039411A1/en not_active Ceased
- 1996-06-05 HU HU9802662A patent/HU221342B1/hu unknown
- 1996-06-05 TW TW085106735A patent/TW366345B/zh not_active IP Right Cessation
- 1996-06-05 CN CN96195890A patent/CN1067082C/zh not_active Expired - Lifetime
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1997
- 1997-12-04 MX MX9709502A patent/MX9709502A/es unknown
- 1997-12-04 NO NO19975644A patent/NO310239B1/no not_active IP Right Cessation
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1999
- 1999-04-16 US US09/293,856 patent/US6184366B1/en not_active Expired - Lifetime
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2001
- 2001-01-30 US US09/774,541 patent/US20020028927A1/en not_active Abandoned
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2002
- 2002-05-13 US US10/144,670 patent/US20030144503A1/en not_active Abandoned
- 2002-06-02 IL IL149971A patent/IL149971A/en not_active IP Right Cessation
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2007
- 2007-06-11 JP JP2007154127A patent/JP4712001B2/ja not_active Expired - Lifetime
- 2007-07-30 US US11/830,412 patent/US7737129B2/en not_active Expired - Fee Related
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2010
- 2010-05-17 US US12/781,166 patent/US7994154B2/en not_active Expired - Fee Related
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2011
- 2011-01-31 JP JP2011018401A patent/JP2011121970A/ja active Pending
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