JP2013525431A5 - - Google Patents
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- JP2013525431A5 JP2013525431A5 JP2013507951A JP2013507951A JP2013525431A5 JP 2013525431 A5 JP2013525431 A5 JP 2013525431A5 JP 2013507951 A JP2013507951 A JP 2013507951A JP 2013507951 A JP2013507951 A JP 2013507951A JP 2013525431 A5 JP2013525431 A5 JP 2013525431A5
- Authority
- JP
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- Prior art keywords
- alkyl
- substituted
- composition
- item
- alkoxy
- 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.)
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- 239000000203 mixture Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 14
- 150000003904 phospholipids Chemical class 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- -1 substituted Chemical class 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 230000001629 suppression Effects 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 230000033444 hydroxylation Effects 0.000 claims description 2
- 238000005805 hydroxylation reaction Methods 0.000 claims description 2
- 230000028993 immune response Effects 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002811 oleoyl 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])=C([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 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 241000193738 Bacillus anthracis Species 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229940065181 bacillus anthracis Drugs 0.000 claims 2
- MWRBNPKJOOWZPW-NYVOMTAGSA-N 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine zwitterion Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-NYVOMTAGSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 description 45
- 239000000427 antigen Substances 0.000 description 11
- 102000036639 antigens Human genes 0.000 description 11
- 108091007433 antigens Proteins 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 8
- 244000005700 microbiome Species 0.000 description 5
- MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000232 Lipid Bilayer Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 210000004215 spore Anatomy 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- ZMEIFBXKYSTSCH-POMHRFKHSA-N CC(OC[C@H](COP(OC)(OCCNC(c1ccc(CN(c2nc(OCCOC)nc(N)c2N2)C2=O)cc1)=O)=O)OC(C)=O)=O Chemical compound CC(OC[C@H](COP(OC)(OCCNC(c1ccc(CN(c2nc(OCCOC)nc(N)c2N2)C2=O)cc1)=O)=O)OC(C)=O)=O ZMEIFBXKYSTSCH-POMHRFKHSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000029662 T-helper 1 type immune response Effects 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 210000004666 bacterial spore Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 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 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000029069 type 2 immune response Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34357310P | 2010-04-30 | 2010-04-30 | |
| US61/343,573 | 2010-04-30 | ||
| PCT/US2011/000757 WO2011139348A2 (en) | 2010-04-30 | 2011-04-29 | Uses of phospholipid conjugates of synthetic tlr7 agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013525431A JP2013525431A (ja) | 2013-06-20 |
| JP2013525431A5 true JP2013525431A5 (enExample) | 2014-05-08 |
Family
ID=44904283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013507951A Pending JP2013525431A (ja) | 2010-04-30 | 2011-04-29 | 合成ｔｌｒ７アゴニストのリン脂質結合体の使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20130202629A1 (enExample) |
| EP (1) | EP2563366A4 (enExample) |
| JP (1) | JP2013525431A (enExample) |
| CN (1) | CN103118682A (enExample) |
| WO (1) | WO2011139348A2 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101304748A (zh) | 2005-08-22 | 2008-11-12 | 加利福尼亚大学董事会 | Tlr激动剂 |
| EP2700638A1 (en) | 2006-05-31 | 2014-02-26 | The Regents Of the University of California | Purine analogs |
| HUE025555T2 (en) | 2007-02-07 | 2016-02-29 | Univ California | Conjugates and applications of synthetic tlr agonists |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| EP2396328A2 (en) * | 2009-02-11 | 2011-12-21 | The Regents of The University of California | Toll-like receptor modulators and treatment of diseases |
| EP2674170B1 (en) | 2012-06-15 | 2014-11-19 | Invivogen | Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids |
| WO2014052828A1 (en) | 2012-09-27 | 2014-04-03 | The Regents Of The University Of California | Compositions and methods for modulating tlr4 |
| US9295732B2 (en) | 2013-02-22 | 2016-03-29 | Invivogen | Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists |
| WO2015023858A2 (en) * | 2013-08-16 | 2015-02-19 | The Regents Of The University Of California | Uses of phospholipid conjugates of synthetic tlr7 agonists |
| ES2804101T3 (es) | 2014-04-22 | 2021-02-03 | Hoffmann La Roche | Compuestos de 4-amino-imidazoquinolina |
| PT3265458T (pt) | 2015-03-06 | 2019-02-13 | Hoffmann La Roche | Compostos de dicarboxamida de benzazepina |
| WO2017046112A1 (en) | 2015-09-17 | 2017-03-23 | F. Hoffmann-La Roche Ag | Sulfinylphenyl or sulfonimidoylphenyl benzazepines |
| EP3355933B1 (en) * | 2015-09-29 | 2020-05-06 | Sumitomo Dainippon Pharma Co., Ltd. | Adenine conjugate compounds and their use as vaccine adjuvants |
| CN108290845B (zh) | 2015-10-07 | 2021-08-03 | 大日本住友制药株式会社 | 嘧啶化合物 |
| JP6918838B2 (ja) | 2016-05-23 | 2021-08-11 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | 第三級アミド基を有するベンズアゼピンジカルボキサミド化合物 |
| JP7022702B2 (ja) | 2016-05-23 | 2022-02-18 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | 第二級アミド基を有するベンズアゼピンジカルボキサミド化合物 |
| US11697851B2 (en) | 2016-05-24 | 2023-07-11 | The Regents Of The University Of California | Early ovarian cancer detection diagnostic test based on mRNA isoforms |
| WO2017216054A1 (en) | 2016-06-12 | 2017-12-21 | F. Hoffmann-La Roche Ag | Dihydropyrimidinyl benzazepine carboxamide compounds |
| US20200087625A1 (en) * | 2017-03-30 | 2020-03-19 | Dennis A. Carson | Methods for isolating, expanding and administering cancer specific cd8+ t cells |
| AR111651A1 (es) * | 2017-04-28 | 2019-08-07 | Novartis Ag | Conjugados de anticuerpos que comprenden agonistas del receptor de tipo toll y terapias de combinación |
| US10494370B2 (en) | 2017-08-16 | 2019-12-03 | Bristol-Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having a pyridine or pyrazine moiety, conjugates thereof, and methods and uses therefor |
| US10457681B2 (en) | 2017-08-16 | 2019-10-29 | Bristol_Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having a tricyclic moiety, conjugates thereof, and methods and uses therefor |
| US10508115B2 (en) | 2017-08-16 | 2019-12-17 | Bristol-Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having heteroatom-linked aromatic moieties, conjugates thereof, and methods and uses therefor |
| US10472361B2 (en) | 2017-08-16 | 2019-11-12 | Bristol-Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having a benzotriazole moiety, conjugates thereof, and methods and uses therefor |
| US10487084B2 (en) | 2017-08-16 | 2019-11-26 | Bristol-Myers Squibb Company | Toll-like receptor 7 (TLR7) agonists having a heterobiaryl moiety, conjugates thereof, and methods and uses therefor |
| US11485741B2 (en) | 2018-04-24 | 2022-11-01 | Bristol-Myers Squibb Company | Macrocyclic toll-like receptor 7 (TLR7) agonists |
| AU2019299609B9 (en) | 2018-07-03 | 2024-07-11 | Jiangsu Hengrui Medicine Co., Ltd. | Pyridopyrimidine derivative, preparation method therefor and medical use thereof |
| GB201811169D0 (en) * | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| MX2021000951A (es) | 2018-07-23 | 2021-06-23 | Sumitomo Pharma Co Ltd | Composición que contiene vacuna contra la influenza. |
| US11554120B2 (en) | 2018-08-03 | 2023-01-17 | Bristol-Myers Squibb Company | 1H-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (TLR7) agonists and methods and uses therefor |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| WO2020141223A1 (en) * | 2019-01-04 | 2020-07-09 | Ascendis Pharma A/S | Induction of sustained local inflammation |
| CA3140708A1 (en) | 2019-06-18 | 2020-12-24 | Helen Horton | Combination of hepatitis b virus (hbv) vaccines and pyridopyrimidine derivatives |
| CN114514015B (zh) | 2019-09-19 | 2025-01-07 | 丹麦科技大学 | 免疫刺激胶束组合物 |
| AU2020407871A1 (en) * | 2019-12-20 | 2022-06-30 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing toll-like receptor ("TLR") agonist prodrugs useful in the treatment of cancer and methods thereof |
| WO2021136488A1 (zh) | 2020-01-02 | 2021-07-08 | 江苏恒瑞医药股份有限公司 | 一种吡啶并嘧啶类衍生物的结晶形式及其制备方法 |
| KR20220132594A (ko) | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
| US20230127326A1 (en) | 2020-01-27 | 2023-04-27 | Bristol-Myers Squibb Company | C3-SUBSTITUTED 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| WO2021154661A1 (en) | 2020-01-27 | 2021-08-05 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| JP2023512208A (ja) | 2020-01-27 | 2023-03-24 | ブリストル－マイヤーズ スクイブ カンパニー | トール様受容体７（ＴＬＲ７）アゴニストとしての１Ｈ－ピラゾロ［４，３－ｄ］ピリミジン化合物 |
| KR20220132590A (ko) | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
| EP4097106A1 (en) | 2020-01-27 | 2022-12-07 | Bristol-Myers Squibb Company | 1h-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (tlr7) agonists |
| US20230131192A1 (en) | 2020-01-27 | 2023-04-27 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| US20230122249A1 (en) | 2020-01-27 | 2023-04-20 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| CN115151548A (zh) | 2020-01-27 | 2022-10-04 | 百时美施贵宝公司 | 作为Toll样受体7(TLR7)激动剂的1H-吡唑并[4,3-d]嘧啶化合物 |
| CN118724963A (zh) * | 2023-03-30 | 2024-10-01 | 浙江养生堂天然药物研究所有限公司 | 含磷或含硫的大环化合物及其用途 |
| WO2024250985A1 (zh) * | 2023-06-07 | 2024-12-12 | 上海维申医药有限公司 | Toll样受体激动剂杂环类衍生物及其制备和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050158325A1 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Immunomodulatory combinations |
| DE602005025342D1 (de) * | 2004-05-28 | 2011-01-27 | Glaxosmithkline Biolog Sa | Impfstoffzusammensetzungen mit virosomen und einem saponin-adjuvans |
| KR20080006004A (ko) * | 2005-05-04 | 2008-01-15 | 화이자 리미티드 | 암 및 ｃ형 간염과 같은 바이러스 감염의 치료를 위한톨-유사 수용체 조절제인 2-아미도-6-아미노-8-옥소퓨린유도체 |
| US8338593B2 (en) * | 2006-07-07 | 2012-12-25 | Gilead Sciences, Inc. | Modulators of toll-like receptor 7 |
| US20090181078A1 (en) * | 2006-09-26 | 2009-07-16 | Infectious Disease Research Institute | Vaccine composition containing synthetic adjuvant |
| HUE025555T2 (en) * | 2007-02-07 | 2016-02-29 | Univ California | Conjugates and applications of synthetic tlr agonists |
| EP2396328A2 (en) * | 2009-02-11 | 2011-12-21 | The Regents of The University of California | Toll-like receptor modulators and treatment of diseases |
| EP2563401A1 (en) * | 2010-04-30 | 2013-03-06 | Telormedix SA | Methods for inducing an immune response |
| CA2797315C (en) * | 2010-04-30 | 2018-09-11 | Telormedix Sa | Phospholipid drug analogs |
-
2011
- 2011-04-29 US US13/695,385 patent/US20130202629A1/en not_active Abandoned
- 2011-04-29 JP JP2013507951A patent/JP2013525431A/ja active Pending
- 2011-04-29 CN CN2011800330222A patent/CN103118682A/zh active Pending
- 2011-04-29 WO PCT/US2011/000757 patent/WO2011139348A2/en not_active Ceased
- 2011-04-29 EP EP11777689.8A patent/EP2563366A4/en not_active Withdrawn
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