JP2019517588A5 - - Google Patents
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- Publication number
- JP2019517588A5 JP2019517588A5 JP2019516096A JP2019516096A JP2019517588A5 JP 2019517588 A5 JP2019517588 A5 JP 2019517588A5 JP 2019516096 A JP2019516096 A JP 2019516096A JP 2019516096 A JP2019516096 A JP 2019516096A JP 2019517588 A5 JP2019517588 A5 JP 2019517588A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- optionally substituted
- och
- alkynyl
- 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
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 65
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 65
- 125000003118 aryl group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 31
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 108091030071 RNAI Proteins 0.000 claims 20
- 239000003795 chemical substances by application Substances 0.000 claims 20
- 230000009368 gene silencing by RNA Effects 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 229910052717 sulfur Inorganic materials 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- -1 amino, hydroxyl Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical group NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- 230000000692 anti-sense effect Effects 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical class CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 229930024421 Adenine Natural products 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- 229930010555 Inosine Natural products 0.000 claims 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims 1
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims 1
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229960000643 adenine Drugs 0.000 claims 1
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 1
- 229940104302 cytosine Drugs 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229960003786 inosine Drugs 0.000 claims 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical group O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims 1
- 229960000367 inositol Drugs 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 125000003729 nucleotide group Chemical group 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003212 purines Chemical class 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 235000021092 sugar substitutes Nutrition 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 229940113082 thymine Drugs 0.000 claims 1
- 229940035893 uracil Drugs 0.000 claims 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022022652A JP7530927B2 (ja) | 2016-06-06 | 2022-02-17 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
| JP2024074835A JP2024097860A (ja) | 2016-06-06 | 2024-05-02 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662346304P | 2016-06-06 | 2016-06-06 | |
| US62/346,304 | 2016-06-06 | ||
| PCT/US2017/036108 WO2017214112A1 (en) | 2016-06-06 | 2017-06-06 | 5'-cyclo-phosphonate modified nucleotides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022022652A Division JP7530927B2 (ja) | 2016-06-06 | 2022-02-17 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019517588A JP2019517588A (ja) | 2019-06-24 |
| JP2019517588A5 true JP2019517588A5 (cg-RX-API-DMAC7.html) | 2020-07-16 |
| JP7028865B2 JP7028865B2 (ja) | 2022-03-02 |
Family
ID=60579042
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019516096A Active JP7028865B2 (ja) | 2016-06-06 | 2017-06-06 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
| JP2022022652A Active JP7530927B2 (ja) | 2016-06-06 | 2022-02-17 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
| JP2024074835A Pending JP2024097860A (ja) | 2016-06-06 | 2024-05-02 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022022652A Active JP7530927B2 (ja) | 2016-06-06 | 2022-02-17 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
| JP2024074835A Pending JP2024097860A (ja) | 2016-06-06 | 2024-05-02 | ５’－シクロ－ホスホン酸修飾ヌクレオチド |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US11078227B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3464313A4 (cg-RX-API-DMAC7.html) |
| JP (3) | JP7028865B2 (cg-RX-API-DMAC7.html) |
| KR (2) | KR102639586B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN109526222B (cg-RX-API-DMAC7.html) |
| AU (3) | AU2017279512B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3023764A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA201892285A1 (cg-RX-API-DMAC7.html) |
| IL (2) | IL290633B2 (cg-RX-API-DMAC7.html) |
| MX (2) | MX2018015109A (cg-RX-API-DMAC7.html) |
| TW (2) | TW202423483A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2017214112A1 (cg-RX-API-DMAC7.html) |
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| US11015198B2 (en) | 2017-04-05 | 2021-05-25 | Silence Therapeutics Gmbh | Products and compositions |
| CN118267396A (zh) | 2017-10-04 | 2024-07-02 | 艾维迪提生物科学公司 | 核酸-多肽组合物及其用途 |
| AU2020289464B2 (en) * | 2019-06-06 | 2025-12-04 | Avidity Biosciences, Inc. | Nucleic acid-polypeptide compositions and uses thereof |
| KR20230064620A (ko) | 2020-09-11 | 2023-05-10 | 애로우헤드 파마슈티컬스 인코포레이티드 | DUX4의 발현을 억제하기 위한 RNAi 작용제, 그의 조성물, 및 사용 방법 |
| TW202242111A (zh) | 2020-12-18 | 2022-11-01 | 美商Ionis製藥公司 | 用於調節因子ｘｉｉ之化合物及方法 |
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| IL308883A (en) | 2021-05-28 | 2024-01-01 | Arrowhead Pharmaceuticals Inc | RNAi AGENTS FOR INHIBITING EXPRESSION OF MUCIN 5AC (MUC5AC), COMPOSITIONS THEREOF, AND METHODS OF USE |
| MX2024001581A (es) | 2021-08-05 | 2024-04-18 | Sanegene Bio Usa Inc | Derivados de ribosa modificados con 1'-alquilo y metodos de uso. |
| CA3233113A1 (en) | 2021-09-22 | 2023-03-30 | Sanegene Bio Usa Inc. | 2'-alkyl or 3'-alkyl modified ribose derivatives for use in the in-vivo delivery of oligonucleotides |
| US20230227480A1 (en) | 2021-10-05 | 2023-07-20 | Sanegene Bio Usa Inc. | Polyhydroxylated cyclopentane derivatives and methods of use |
| US20230346819A1 (en) | 2022-02-22 | 2023-11-02 | Sanegene Bio Usa Inc. | 5'-modified carbocyclic ribonucleotide derivatives and methods of use |
| WO2023220561A1 (en) | 2022-05-09 | 2023-11-16 | Sanegene Bio Usa Inc. | Double stranded rna targeting 17-beta hydroxysteroiddehydrogenase 13 (hsd17b13) and methods of use thereof |
| AU2023295010A1 (en) * | 2022-06-14 | 2025-01-09 | Rona Bioscience, Limited | Cyclic phosphonate-modified nucleotide |
| JP2025522433A (ja) | 2022-06-15 | 2025-07-15 | アローヘッド ファーマシューティカルズ インコーポレイテッド | スーパーオキシドジスムターゼ１（ＳＯＤ１）の発現を阻害するためのＲＮＡｉ剤、その組成物、及び使用の方法 |
| US20240218363A1 (en) | 2022-07-11 | 2024-07-04 | Sanegene Bio Usa Inc. | Optimized 2'- modified ribose derivatives and methods of use |
| KR20250046303A (ko) | 2022-08-05 | 2025-04-02 | 사네진 바이오 유에스에이 인크. | 안지오텐시노겐 (agt)을 표적화하는 이중 가닥 rna 및 그의 사용 방법 |
| CN119894915A (zh) * | 2022-09-21 | 2025-04-25 | 詹森生物科技公司 | 新型稳定的核苷磷酸及其类似物 |
| JP2025534701A (ja) | 2022-10-14 | 2025-10-17 | セーンジーン バイオ ユーエスエー インコーポレイティド | Ｃ３を標的とする低分子干渉ｒｎａおよびその使用 |
| EP4612294A2 (en) * | 2022-11-02 | 2025-09-10 | Aligos Therapeutics, Inc. | Modified short interfering nucleic acid (sina) molecules and uses thereof |
| JP2025542234A (ja) | 2022-12-19 | 2025-12-25 | セーンジーン バイオ ユーエスエー インコーポレイティド | 低分子干渉ｒｎａ標的化ｃｆｂ及びその使用 |
| WO2024175111A2 (en) | 2023-02-24 | 2024-08-29 | Suzhou Sanegene Bio Inc. | Small interfering rna targeting hbv and uses thereof |
| WO2024186673A2 (en) | 2023-03-03 | 2024-09-12 | Sanegene Bio Usa Inc. | Small interfering rna targeting apoc3 and uses thereof |
| AU2024240837A1 (en) | 2023-03-21 | 2025-09-11 | Arrowhead Pharmaceuticals, Inc. | Rnai agents for inhibiting expression of complement factor b (cfb) pharmaceutical compositions thereof, and methods of use |
| KR20250174651A (ko) * | 2023-04-06 | 2025-12-12 | 상하이 아르고 바이오파마슈티칼 씨오., 엘티디. | 5'-포스포네이트 변형 뉴클레오시드 유사체 및 이로부터 제조된 올리고뉴클레오티드 |
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2017
- 2017-06-06 CN CN201780034726.9A patent/CN109526222B/zh active Active
- 2017-06-06 JP JP2019516096A patent/JP7028865B2/ja active Active
- 2017-06-06 AU AU2017279512A patent/AU2017279512B2/en active Active
- 2017-06-06 IL IL290633A patent/IL290633B2/en unknown
- 2017-06-06 EA EA201892285A patent/EA201892285A1/ru unknown
- 2017-06-06 CA CA3023764A patent/CA3023764A1/en active Pending
- 2017-06-06 TW TW112132145A patent/TW202423483A/zh unknown
- 2017-06-06 TW TW106118757A patent/TWI815794B/zh active
- 2017-06-06 MX MX2018015109A patent/MX2018015109A/es unknown
- 2017-06-06 KR KR1020227025704A patent/KR102639586B1/ko active Active
- 2017-06-06 WO PCT/US2017/036108 patent/WO2017214112A1/en not_active Ceased
- 2017-06-06 CN CN202210360585.2A patent/CN114736256B/zh active Active
- 2017-06-06 EP EP17810836.1A patent/EP3464313A4/en active Pending
- 2017-06-06 KR KR1020187034959A patent/KR102426487B1/ko active Active
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2023
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