JPWO2020118060A5 - - Google Patents
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- Publication number
- JPWO2020118060A5 JPWO2020118060A5 JP2021531987A JP2021531987A JPWO2020118060A5 JP WO2020118060 A5 JPWO2020118060 A5 JP WO2020118060A5 JP 2021531987 A JP2021531987 A JP 2021531987A JP 2021531987 A JP2021531987 A JP 2021531987A JP WO2020118060 A5 JPWO2020118060 A5 JP WO2020118060A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- compound
- pharmaceutically acceptable
- acceptable salt
- 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
- 150000001875 compounds Chemical class 0.000 claims description 214
- 229910052739 hydrogen Inorganic materials 0.000 claims description 166
- 239000001257 hydrogen Substances 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- 150000003839 salts Chemical class 0.000 claims description 146
- 150000002431 hydrogen Chemical class 0.000 claims description 109
- 125000000623 heterocyclic group Chemical group 0.000 claims description 104
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 60
- 125000000304 alkynyl group Chemical group 0.000 claims description 60
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000004429 atom Chemical group 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 208000024714 major depressive disease Diseases 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 201000009916 Postpartum depression Diseases 0.000 claims description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 2
- 208000029560 autism spectrum disease Diseases 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000036407 pain Effects 0.000 claims description 2
- 208000022821 personality disease Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 208000005809 status epilepticus Diseases 0.000 claims description 2
- 201000009032 substance abuse Diseases 0.000 claims description 2
- 231100000736 substance abuse Toxicity 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 231100000886 tinnitus Toxicity 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 206010044565 Tremor Diseases 0.000 claims 2
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010039897 Sedation Diseases 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 201000006517 essential tremor Diseases 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000036280 sedation Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 5
- 230000017105 transposition Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024077572A JP7720948B2 (ja) | 2018-12-05 | 2024-05-10 | 神経刺激性ステロイド及びその使用方法 |
| JP2025099700A JP2025134803A (ja) | 2018-12-05 | 2025-06-13 | 神経刺激性ステロイド及びその使用方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862775470P | 2018-12-05 | 2018-12-05 | |
| US62/775,470 | 2018-12-05 | ||
| PCT/US2019/064692 WO2020118060A1 (en) | 2018-12-05 | 2019-12-05 | Neuroactive steroids and their methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024077572A Division JP7720948B2 (ja) | 2018-12-05 | 2024-05-10 | 神経刺激性ステロイド及びその使用方法 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022510683A JP2022510683A (ja) | 2022-01-27 |
| JPWO2020118060A5 true JPWO2020118060A5 (https=) | 2022-12-01 |
| JP2022510683A5 JP2022510683A5 (https=) | 2022-12-01 |
| JP7539378B2 JP7539378B2 (ja) | 2024-08-23 |
Family
ID=69006056
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021531987A Active JP7539378B2 (ja) | 2018-12-05 | 2019-12-05 | 神経刺激性ステロイド及びその使用方法 |
| JP2024077572A Active JP7720948B2 (ja) | 2018-12-05 | 2024-05-10 | 神経刺激性ステロイド及びその使用方法 |
| JP2025099700A Pending JP2025134803A (ja) | 2018-12-05 | 2025-06-13 | 神経刺激性ステロイド及びその使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024077572A Active JP7720948B2 (ja) | 2018-12-05 | 2024-05-10 | 神経刺激性ステロイド及びその使用方法 |
| JP2025099700A Pending JP2025134803A (ja) | 2018-12-05 | 2025-06-13 | 神経刺激性ステロイド及びその使用方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (8) | US20230322846A9 (https=) |
| EP (1) | EP3902818A1 (https=) |
| JP (3) | JP7539378B2 (https=) |
| KR (2) | KR20250174100A (https=) |
| CN (1) | CN113383004A (https=) |
| AR (1) | AR117264A1 (https=) |
| AU (3) | AU2019392680B2 (https=) |
| BR (1) | BR112021010996A2 (https=) |
| CA (1) | CA3120872A1 (https=) |
| IL (3) | IL283629B2 (https=) |
| MA (1) | MA54594A (https=) |
| MX (4) | MX2021006618A (https=) |
| TW (2) | TW202521127A (https=) |
| WO (1) | WO2020118060A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG10201606063RA (en) | 2012-01-23 | 2016-09-29 | Sage Therapeutics Inc | Neuroactive steroid formulations and methods of treating cns disorders |
| MX2015002252A (es) | 2012-08-21 | 2015-07-21 | Sage Therapeutics Inc | Metodos para tratar epilepsia o estado de epilepsia. |
| JP6470258B2 (ja) | 2013-04-17 | 2019-02-13 | セージ セラピューティクス， インコーポレイテッド | １９−ノルｃ３，３−ジ置換ｃ２１−ｎ−ピラゾリルステロイドおよびその使用方法 |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| JOP20200195A1 (ar) | 2014-09-08 | 2017-06-16 | Sage Therapeutics Inc | سترويدات وتركيبات نشطة عصبياً، واستخداماتها |
| WO2016082789A1 (en) | 2014-11-27 | 2016-06-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| TWI904593B (zh) | 2016-08-23 | 2025-11-11 | 美商賽吉醫療公司 | 結晶19-去甲c3,3-二取代之c21-n-吡唑類固醇 |
| EP3720867A1 (en) | 2017-12-08 | 2020-10-14 | Sage Therapeutics, Inc. | Deuterated 21 -[4-cyano-pyrazol-1 -yl]-19-nor-pregan-3. alpha-ol-20-one derivatives for treating cns disorders |
| EP3728284B1 (en) * | 2017-12-22 | 2024-08-21 | Sage Therapeutics, Inc. | 19-homo, 3.alpha.-hydroxy-steroid-20-one compounds for treating cns disorders |
| MA51568A (fr) | 2018-01-12 | 2021-04-21 | Sage Therapeutics Inc | Composés aza-, oxa et thia-pregnan-20-one-3.alpha.-ol s'utilisant dans le traitement de troubles du système nerveux central |
| CN113195512A (zh) * | 2018-12-21 | 2021-07-30 | 萨奇治疗股份有限公司 | 3.α.-羟基-17.β.-酰胺神经活性类固醇及其组合物 |
| CR20240234A (es) * | 2019-05-31 | 2024-07-09 | Sage Therapeutics Inc | ESTEROIDES NEUROACTIVOS Y COMPOSICIONES DE ESTOS (Divisional 2021-629) |
| JP7787635B2 (ja) * | 2019-06-27 | 2025-12-17 | セージ セラピューティクス， エルエルシー | Ｃｎｓ障害を治療するための組成物及び方法 |
| US20230257415A1 (en) * | 2019-06-27 | 2023-08-17 | Sage Therapeutics, Inc. | Compounds for treating cns disorders |
| TW202143976A (zh) * | 2020-03-18 | 2021-12-01 | 美商賽吉醫療公司 | 神經活性類固醇及其使用方法 |
| CN112679571A (zh) * | 2020-12-24 | 2021-04-20 | 广西壮族自治区中国科学院广西植物研究所 | 一种罗汉果醇衍生物单体、其制备方法及应用 |
| JP2024532273A (ja) * | 2021-08-25 | 2024-09-05 | セージ セラピューティクス， インコーポレイテッド | ポジティブｎｍｄａモジュレート化合物及びその使用方法 |
| CN115974950A (zh) * | 2022-12-23 | 2023-04-18 | 上海彩迩文生化科技有限公司 | 一种3-烷基化的甾体中间体及其制备和应用 |
| KR20250162825A (ko) | 2023-03-14 | 2025-11-19 | 쿠리아 스페인, 에스.에이.유. | 3알파-하이드록시-3베타-알킬 스테로이드의 제조를 위한 방법 및 중간체 |
| WO2024197317A2 (en) * | 2023-03-23 | 2024-09-26 | Emory University | Neurosteroids and prodrugs thereof |
| CN119529013B (zh) * | 2024-11-25 | 2025-11-07 | 湖南新合新生物医药有限公司 | 一种祖拉诺龙中间体的合成方法 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2969M (fr) * | 1963-05-22 | 1964-11-30 | Roussel Uclaf | Nouveau médicament notamment pour le traitement des spasmes d'origine coronarienne on viscérale. |
| ES432106A1 (es) | 1973-11-30 | 1976-11-01 | Schering Ag | Procedimiento para la preparacion de d-homo-20-cetopregna- nos. |
| IL48628A0 (en) | 1974-12-23 | 1976-02-29 | Schering Ag | D-homo-20-keto-pregnanes and process for their manufactur |
| GB1570394A (en) | 1976-01-06 | 1980-07-02 | Glaxo Lab Ltd | 11-acyloxy-3-hydroxy steroids |
| US4060295A (en) | 1976-03-15 | 1977-11-29 | Molex Incorporated | Zero insertion force printed circuit board edge connector assembly |
| GB1581234A (en) | 1976-04-05 | 1980-12-10 | Glaxo Operations Ltd | 11a - amino - 3a - hydroxysteroids |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US5939545A (en) | 1994-02-14 | 1999-08-17 | Cocensys, Inc. | Method, compositions, and compounds for allosteric modulation of the gaba receptor by members of the androstane and pregnane series |
| FI972202L (fi) * | 1994-11-23 | 1997-07-17 | Cocensys Inc | Androstaanit ja pregnaanit GABA-reseptoreiden allosteeriseen muunteluun |
| AU3967297A (en) * | 1996-08-01 | 1998-02-25 | Cocensys, Inc. | Use of gaba and nmda receptor ligands for the treatment of migraine headache |
| US8569275B2 (en) | 2002-08-28 | 2013-10-29 | Harbor Therapeutics, Inc. | Steroids having 7-oxgen and 17-heteroaryl substitution |
| FR2967914A1 (fr) | 2010-11-29 | 2012-06-01 | Centre Nat Rech Scient | Composes inhibiteurs d'interactions proteine-proteine ciblant les proteines kinases et leurs applications biologiques |
| CN119192266A (zh) | 2011-10-14 | 2024-12-27 | 萨奇治疗股份有限公司 | 3,3-二取代的19-去甲孕甾烷化合物、组合物、及其用途 |
| WO2014169831A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor c3,3-disubstituted c21-c-bound heteroaryl steroids and methods of use thereof |
| JP6470258B2 (ja) | 2013-04-17 | 2019-02-13 | セージ セラピューティクス， インコーポレイテッド | １９−ノルｃ３，３−ジ置換ｃ２１−ｎ−ピラゾリルステロイドおよびその使用方法 |
| US10577390B2 (en) | 2014-10-16 | 2020-03-03 | Sage Therapeutics, Inc. | Compositions and methods for treating CNS disorders |
| WO2017049044A1 (en) * | 2015-09-16 | 2017-03-23 | Bartolucci Giampiero | Ursodeoxycholic acid and brain disorders |
| WO2017187343A2 (en) | 2016-04-29 | 2017-11-02 | Thome Kreutz Fernando | Nanoemulsions and methods for cancer therapy |
| MA45599A (fr) | 2016-07-11 | 2019-05-15 | Sage Therapeutics Inc | Stéroïdes neuroactifs substitués en c17, c20 et c21 et leurs procédés d'utilisation |
| TWI904593B (zh) | 2016-08-23 | 2025-11-11 | 美商賽吉醫療公司 | 結晶19-去甲c3,3-二取代之c21-n-吡唑類固醇 |
| CN108727453A (zh) | 2017-04-20 | 2018-11-02 | 华东理工大学 | 新型pd-1抑制剂及其应用 |
| CN111741965B (zh) | 2017-12-22 | 2024-06-25 | 萨奇治疗股份有限公司 | 治疗中枢神经系统疾病的组合物和方法 |
| US20200384003A1 (en) | 2017-12-29 | 2020-12-10 | Shanghai Lanmu Chemicals Co., Ltd. | Triterpenoid-containing pharmaceutical composition and use thereof |
| CN114656514B (zh) | 2018-02-11 | 2024-05-14 | 江苏豪森药业集团有限公司 | 一种甾族类衍生物调节剂及其制备方法和应用 |
| EP3852764A4 (en) | 2018-09-19 | 2022-06-15 | ModernaTX, Inc. | STEROL ANALOGUES AND USES THEREOF |
| CN113195512A (zh) | 2018-12-21 | 2021-07-30 | 萨奇治疗股份有限公司 | 3.α.-羟基-17.β.-酰胺神经活性类固醇及其组合物 |
| WO2020210117A1 (en) | 2019-04-08 | 2020-10-15 | Athenen Therapeutics, Inc. | Steroids with altered pharmacokinetic properties and methods of use thereof |
| WO2020210116A1 (en) | 2019-04-08 | 2020-10-15 | Athenen Therapeutics, Inc. | Steroids with altered pharmacokinetic properties and methods of use thereof |
| CN114144185A (zh) | 2019-05-30 | 2022-03-04 | 英特塞普特医药品公司 | 用于治疗胆汁淤积性肝病的包含fxr激动剂和贝特类的药物组合物 |
| CR20240234A (es) | 2019-05-31 | 2024-07-09 | Sage Therapeutics Inc | ESTEROIDES NEUROACTIVOS Y COMPOSICIONES DE ESTOS (Divisional 2021-629) |
| US20230257415A1 (en) | 2019-06-27 | 2023-08-17 | Sage Therapeutics, Inc. | Compounds for treating cns disorders |
| US20220396597A1 (en) | 2019-10-25 | 2022-12-15 | Washington University | Nmdar inhibiting agents and gabaar potentiating agents and uses thereof |
| IL299176A (en) | 2020-06-24 | 2023-02-01 | Sage Therapeutics Inc | 3.alpha.-hydroxy, 17.beta.-c(o)-n-aryl substituted neuroactive steroids and compositions thereof |
-
2019
- 2019-12-05 IL IL283629A patent/IL283629B2/en unknown
- 2019-12-05 BR BR112021010996-0A patent/BR112021010996A2/pt unknown
- 2019-12-05 TW TW114104450A patent/TW202521127A/zh unknown
- 2019-12-05 IL IL312610A patent/IL312610B1/en unknown
- 2019-12-05 EP EP19828126.3A patent/EP3902818A1/en active Pending
- 2019-12-05 MX MX2021006618A patent/MX2021006618A/es unknown
- 2019-12-05 WO PCT/US2019/064692 patent/WO2020118060A1/en not_active Ceased
- 2019-12-05 CN CN201980091069.0A patent/CN113383004A/zh active Pending
- 2019-12-05 MA MA054594A patent/MA54594A/fr unknown
- 2019-12-05 KR KR1020257039569A patent/KR20250174100A/ko active Pending
- 2019-12-05 CA CA3120872A patent/CA3120872A1/en active Pending
- 2019-12-05 KR KR1020217020784A patent/KR102892974B1/ko active Active
- 2019-12-05 JP JP2021531987A patent/JP7539378B2/ja active Active
- 2019-12-05 US US17/311,056 patent/US20230322846A9/en not_active Abandoned
- 2019-12-05 TW TW108144589A patent/TWI874337B/zh active
- 2019-12-05 AU AU2019392680A patent/AU2019392680B2/en active Active
- 2019-12-05 IL IL312611A patent/IL312611B2/en unknown
- 2019-12-06 AR ARP190103566A patent/AR117264A1/es unknown
-
2021
- 2021-06-03 MX MX2024004789A patent/MX2024004789A/es unknown
- 2021-06-03 MX MX2024004788A patent/MX2024004788A/es unknown
- 2021-06-03 MX MX2024004790A patent/MX2024004790A/es unknown
-
2023
- 2023-06-13 US US18/334,124 patent/US11970514B2/en active Active
- 2023-06-13 US US18/334,189 patent/US11999765B2/en active Active
- 2023-06-13 US US18/334,209 patent/US11912738B2/en active Active
-
2024
- 2024-03-26 US US18/616,762 patent/US12264177B2/en active Active
- 2024-03-26 US US18/616,995 patent/US12410210B2/en active Active
- 2024-03-26 US US18/616,903 patent/US12252509B2/en active Active
- 2024-05-10 JP JP2024077572A patent/JP7720948B2/ja active Active
-
2025
- 2025-01-14 US US19/019,743 patent/US20250154194A1/en active Pending
- 2025-05-14 AU AU2025203487A patent/AU2025203487A1/en active Pending
- 2025-05-14 AU AU2025203485A patent/AU2025203485A1/en active Pending
- 2025-06-13 JP JP2025099700A patent/JP2025134803A/ja active Pending
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