JPWO2020065408A5 - - Google Patents
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- JPWO2020065408A5 JPWO2020065408A5 JP2021517292A JP2021517292A JPWO2020065408A5 JP WO2020065408 A5 JPWO2020065408 A5 JP WO2020065408A5 JP 2021517292 A JP2021517292 A JP 2021517292A JP 2021517292 A JP2021517292 A JP 2021517292A JP WO2020065408 A5 JPWO2020065408 A5 JP WO2020065408A5
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- Japan
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- alkyl
- arylene
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 229940079593 drug Drugs 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 14
- 125000005647 linker group Chemical group 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000004104 aryloxy group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- -1 4-nitro-phenyloxy, pentafluorophenoxy Chemical group 0.000 claims 8
- 229940044665 STING agonist Drugs 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 239000000427 antigen Substances 0.000 claims 4
- 102000036639 antigens Human genes 0.000 claims 4
- 108091007433 antigens Proteins 0.000 claims 4
- 125000000732 arylene group Chemical group 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- HXCHCVDVKSCDHU-PJKCJEBCSA-N s-[(2r,3s,4s,6s)-6-[[(2r,3s,4s,5r,6r)-5-[(2s,4s,5s)-5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2s,5z,9r,13e)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-m Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-PJKCJEBCSA-N 0.000 claims 4
- AGGWFDNPHKLBBV-YUMQZZPRSA-N (2s)-2-[[(2s)-2-amino-3-methylbutanoyl]amino]-5-(carbamoylamino)pentanoic acid Chemical group CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=O AGGWFDNPHKLBBV-YUMQZZPRSA-N 0.000 claims 3
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| CN104230916B (zh) * | 2014-09-30 | 2020-04-28 | 上海化学试剂研究所有限公司 | 一种异噻唑啉酮类化合物及其制备方法和应用 |
| EP3209334A2 (en) * | 2014-10-20 | 2017-08-30 | Igenica Biotherapeutics, Inc. | Novel antibody-drug conjugates and related compounds, compositions, and methods of use |
| EP3546473B1 (en) | 2014-12-16 | 2025-12-10 | Kayla Therapeutics | Fluorinated cyclic [(2',5')p(3',5')p]-dinucleotides for cytokine induction |
| HK1248603A1 (zh) | 2015-03-10 | 2018-10-19 | Aduro Biotech, Inc. | 用於活化"干扰素基因的刺激剂"依懒性信号传导的组合物和方法 |
| CN112125929A (zh) | 2015-06-15 | 2020-12-25 | 杭州多禧生物科技有限公司 | 用于偶联的亲水链接体 |
| WO2017051254A1 (en) * | 2015-09-25 | 2017-03-30 | Legochem Biosciences, Inc. | Compositions and methods related to anti-egfr antibody drug conjugates |
| US20180369268A1 (en) | 2015-12-16 | 2018-12-27 | Aduro Biotech, Inc. | Methods for identifying inhibitors of "stimulator of interferon gene"- dependent interferon production |
| MY195114A (en) * | 2016-02-04 | 2023-01-10 | Robert Yongxin Zhao | Specific Conjugation Linkers, Specific Immunoconjugates Thereof, Methods of Making and uses Such Conjugates Thereof |
| WO2018100558A2 (en) | 2016-12-01 | 2018-06-07 | Takeda Pharmaceutical Company Limited | Cyclic dinucleotide |
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2019
- 2019-09-27 MX MX2021003295A patent/MX2021003295A/es unknown
- 2019-09-27 EP EP19813935.4A patent/EP3856258B1/en active Active
- 2019-09-27 WO PCT/IB2019/001114 patent/WO2020065408A1/en not_active Ceased
- 2019-09-27 US US17/280,800 patent/US12011485B2/en active Active
- 2019-09-27 CA CA3113378A patent/CA3113378C/en active Active
- 2019-09-27 BR BR112021005655-6A patent/BR112021005655A2/pt unknown
- 2019-09-27 AU AU2019350536A patent/AU2019350536B2/en active Active
- 2019-09-27 JP JP2021517292A patent/JP2022502431A/ja active Pending
- 2019-09-27 CN CN201980077950.5A patent/CN113453724B/zh active Active
- 2019-09-27 KR KR1020217012389A patent/KR102858995B1/ko active Active
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2021
- 2021-03-24 ZA ZA2021/01990A patent/ZA202101990B/en unknown
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2024
- 2024-03-29 US US18/622,613 patent/US20240350657A1/en active Pending
- 2024-07-01 JP JP2024106489A patent/JP7830555B2/ja active Active
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