JP2018529717A5 - - Google Patents
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- Publication number
- JP2018529717A5 JP2018529717A5 JP2018516214A JP2018516214A JP2018529717A5 JP 2018529717 A5 JP2018529717 A5 JP 2018529717A5 JP 2018516214 A JP2018516214 A JP 2018516214A JP 2018516214 A JP2018516214 A JP 2018516214A JP 2018529717 A5 JP2018529717 A5 JP 2018529717A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acceptable salt
- antigen
- compound
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 102000036639 antigens Human genes 0.000 claims 16
- 108091007433 antigens Proteins 0.000 claims 16
- 239000000427 antigen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 239000012646 vaccine adjuvant Substances 0.000 claims 8
- 229940124931 vaccine adjuvant Drugs 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 239000007764 o/w emulsion Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims 2
- 244000052769 pathogen Species 0.000 claims 2
- 230000001717 pathogenic effect Effects 0.000 claims 2
- 229920001993 poloxamer 188 Polymers 0.000 claims 2
- 229940044519 poloxamer 188 Drugs 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 229940031439 squalene Drugs 0.000 claims 2
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- KMBRETKMIXPCMR-GITNALPWSA-N 6-amino-2-(2,3-dihydroxypropoxy)-9-[[4-[[[(4E,8E,12E,16E,20E)-4,8,12,17,21,25-hexamethylhexacosa-4,8,12,16,20,24-hexaenyl]-methylamino]methyl]phenyl]methyl]-7H-purin-8-one Chemical compound CN(CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)Cc1ccc(Cn2c3nc(OCC(O)CO)nc(N)c3[nH]c2=O)cc1 KMBRETKMIXPCMR-GITNALPWSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims 1
- 239000004147 Sorbitan trioleate Substances 0.000 claims 1
- ZBNRGEMZNWHCGA-WECPCUOASA-N [(2R)-2-hydroxy-2-[(2R,3R,4S)-4-[(Z)-octadec-9-enoyl]oxy-3-[(E)-octadec-9-enoyl]oxyoxolan-2-yl]ethyl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC(=O)CCCCCCC\C=C\CCCCCCCC ZBNRGEMZNWHCGA-WECPCUOASA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000002619 cancer immunotherapy Methods 0.000 claims 1
- 239000012830 cancer therapeutic Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000003308 immunostimulating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 229960000391 sorbitan trioleate Drugs 0.000 claims 1
- 235000019337 sorbitan trioleate Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562234481P | 2015-09-29 | 2015-09-29 | |
| US62/234,481 | 2015-09-29 | ||
| PCT/JP2016/004375 WO2017056494A1 (en) | 2015-09-29 | 2016-09-28 | Adenine conjugate compounds and their use as vaccine adjuvants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018529717A JP2018529717A (ja) | 2018-10-11 |
| JP2018529717A5 true JP2018529717A5 (https=) | 2019-11-07 |
| JP6764930B2 JP6764930B2 (ja) | 2020-10-07 |
Family
ID=57138095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018516214A Active JP6764930B2 (ja) | 2015-09-29 | 2016-09-28 | アデニンコンジュゲート化合物およびそのワクチンアジュバントとしての使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10597397B2 (https=) |
| EP (1) | EP3355933B1 (https=) |
| JP (1) | JP6764930B2 (https=) |
| CN (1) | CN108348618B (https=) |
| CA (1) | CA2998995A1 (https=) |
| DK (1) | DK3355933T3 (https=) |
| ES (1) | ES2805724T3 (https=) |
| WO (1) | WO2017056494A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108348618B (zh) * | 2015-09-29 | 2021-06-15 | 大日本住友制药株式会社 | 腺嘌呤缀合物化合物及其作为疫苗佐剂的用途 |
| JP2021035910A (ja) * | 2017-11-01 | 2021-03-04 | 大日本住友製薬株式会社 | 置換プリン化合物 |
| CA3107409A1 (en) | 2018-07-23 | 2020-01-30 | Japan As Represented By Director General Of National Institute Of Infectious Diseases | Composition containing influenza vaccine |
| EA202192398A1 (ru) * | 2019-03-04 | 2021-11-23 | Джэпэн Эз Репризентид Баи Директор Дженерал Оф Нэшнл Инститьют Оф Инфекшес Дизизис | Способ приготовления сплит-вакцины против гриппа на основе гемагглютинина |
| WO2020204173A1 (ja) * | 2019-04-05 | 2020-10-08 | 大日本住友製薬株式会社 | 水溶性アジュバントおよびそれを含有する組成物 |
| CN119677745A (zh) * | 2022-07-26 | 2025-03-21 | 酵活英属哥伦比亚有限公司 | 免疫调节剂嘌呤衍生化合物、其缀合物及其使用方法 |
| AU2024249644A1 (en) * | 2023-03-27 | 2025-11-13 | The Cleveland Clinic Foundation | Topical pala therapy for cancer |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| DE69817393T2 (de) | 1997-11-28 | 2004-06-17 | Sumitomo Pharmaceuticals Co., Ltd. | Neue heterozyklische verbindungen |
| US7157465B2 (en) | 2001-04-17 | 2007-01-02 | Dainippon Simitomo Pharma Co., Ltd. | Adenine derivatives |
| JP2007514644A (ja) | 2003-04-10 | 2007-06-07 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応を向上させる方法および組成物 |
| US7799800B2 (en) | 2003-08-14 | 2010-09-21 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| JPWO2007034817A1 (ja) | 2005-09-22 | 2009-03-26 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
| CN101790380B (zh) * | 2007-02-07 | 2013-07-10 | 加利福尼亚大学董事会 | 合成tlr激动剂的缀合物及其应用 |
| AR065784A1 (es) | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
| TR201802083T4 (tr) | 2008-10-24 | 2018-03-21 | Glaxosmithkline Biologicals Sa | Lipidatlı imidazokinolin türevleri. |
| KR20110117705A (ko) | 2009-02-11 | 2011-10-27 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 톨-유사 수용체 조정제 및 질병의 치료 |
| MX2012001524A (es) | 2009-08-07 | 2012-02-29 | Glaxosmithkline Biolog Sa | Derivados de oxoadenina lipidada. |
| JP2013525431A (ja) * | 2010-04-30 | 2013-06-20 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 合成ｔｌｒ７アゴニストのリン脂質結合体の使用 |
| WO2012011606A1 (en) | 2010-07-20 | 2012-01-26 | Dainippon Sumitomo Pharma Co., Ltd. | Process for preparing adenine compounds and intermediates thereof |
| US9242980B2 (en) | 2010-08-17 | 2016-01-26 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
| FR2968662B1 (fr) * | 2010-12-10 | 2013-11-22 | Roussy Inst Gustave | Nouveaux derives d'oxazaphosphorines pre-activees, utilisation et methode de preparation |
| CN108348618B (zh) * | 2015-09-29 | 2021-06-15 | 大日本住友制药株式会社 | 腺嘌呤缀合物化合物及其作为疫苗佐剂的用途 |
-
2016
- 2016-09-28 CN CN201680056561.0A patent/CN108348618B/zh active Active
- 2016-09-28 CA CA2998995A patent/CA2998995A1/en active Pending
- 2016-09-28 EP EP16782095.0A patent/EP3355933B1/en active Active
- 2016-09-28 US US15/763,982 patent/US10597397B2/en active Active
- 2016-09-28 WO PCT/JP2016/004375 patent/WO2017056494A1/en not_active Ceased
- 2016-09-28 DK DK16782095.0T patent/DK3355933T3/da active
- 2016-09-28 JP JP2018516214A patent/JP6764930B2/ja active Active
- 2016-09-28 ES ES16782095T patent/ES2805724T3/es active Active
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