JP2021500335A5 - - Google Patents
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- JP2021500335A5 JP2021500335A5 JP2020521600A JP2020521600A JP2021500335A5 JP 2021500335 A5 JP2021500335 A5 JP 2021500335A5 JP 2020521600 A JP2020521600 A JP 2020521600A JP 2020521600 A JP2020521600 A JP 2020521600A JP 2021500335 A5 JP2021500335 A5 JP 2021500335A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- heteroaryl
- aryl
- optionally
- 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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- -1 Aryl Haloalkyl Chemical group 0.000 claims 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 14
- 229940079593 drug Drugs 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 14
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- KLQLQDLJJUAEGT-ZBFHGGJFSA-N CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC=CC=C1 Chemical compound CO[C@H](C(=O)NC=1SC(=NN=1)N[C@H]1CN(CC1)C=1N=NC=CC=1)C1=CC=CC=C1 KLQLQDLJJUAEGT-ZBFHGGJFSA-N 0.000 claims 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 9
- AJSXCYAUCOGGID-UHFFFAOYSA-N 2-[3-(trifluoromethoxy)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(OC(F)(F)F)=C1 AJSXCYAUCOGGID-UHFFFAOYSA-N 0.000 claims 3
- CUMVNMVSEFYZCA-UHFFFAOYSA-N 2-[4-(3,3-difluorocyclobutyl)oxypyridin-2-yl]acetamide Chemical compound FC1(CC(C1)OC1=CC(=NC=C1)CC(=O)N)F CUMVNMVSEFYZCA-UHFFFAOYSA-N 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- MRFFBSMXJKJPSH-UHFFFAOYSA-N 2-[4-(trifluoromethyl)pyridin-2-yl]acetamide Chemical compound NC(=O)CC1=CC(C(F)(F)F)=CC=N1 MRFFBSMXJKJPSH-UHFFFAOYSA-N 0.000 claims 2
- RUPIXCDIJIZJOH-UHFFFAOYSA-N 2-[4-[3-(trifluoromethoxy)phenyl]pyridin-2-yl]acetamide Chemical compound FC(OC=1C=C(C=CC=1)C1=CC(=NC=C1)CC(=O)N)(F)F RUPIXCDIJIZJOH-UHFFFAOYSA-N 0.000 claims 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
- UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 claims 2
- 102100023927 Asparagine synthetase [glutamine-hydrolyzing] Human genes 0.000 claims 2
- 108010070255 Aspartate-ammonia ligase Proteins 0.000 claims 2
- 108010073324 Glutaminase Proteins 0.000 claims 2
- 102000009127 Glutaminase Human genes 0.000 claims 2
- 101710184006 Glutaminase 1 Proteins 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 2
- 125000006484 halo alkoxy aryl group Chemical group 0.000 claims 2
- 125000006492 halo alkyl aryl group Chemical group 0.000 claims 2
- 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000003106 haloaryl group Chemical group 0.000 claims 2
- 125000002034 haloarylalkyl group Chemical group 0.000 claims 2
- 125000004996 haloaryloxy group Chemical group 0.000 claims 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000005216 haloheteroaryl group Chemical group 0.000 claims 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- ANFPGLWPMQFMAG-UHFFFAOYSA-N 2-(4-cyclopropylpyridin-2-yl)acetamide Chemical compound C1(CC1)C1=CC(=NC=C1)CC(=O)N ANFPGLWPMQFMAG-UHFFFAOYSA-N 0.000 claims 1
- VKQSQZZNPPOUSW-UHFFFAOYSA-N 2-[1-[3-(trifluoromethoxy)phenyl]imidazol-4-yl]acetamide Chemical compound FC(OC=1C=C(C=CC=1)N1C=NC(=C1)CC(=O)N)(F)F VKQSQZZNPPOUSW-UHFFFAOYSA-N 0.000 claims 1
- CCQUVKCOBBJDAM-UHFFFAOYSA-N 2-[4-[cyclopropyl(difluoro)methyl]pyridin-2-yl]acetamide Chemical compound C1(CC1)C(C1=CC(=NC=C1)CC(=O)N)(F)F CCQUVKCOBBJDAM-UHFFFAOYSA-N 0.000 claims 1
- WZCKODVGPQVPJP-UHFFFAOYSA-N 2-[6-methyl-4-(trifluoromethyl)pyridin-2-yl]acetamide Chemical compound CC1=CC(=CC(=N1)CC(=O)N)C(F)(F)F WZCKODVGPQVPJP-UHFFFAOYSA-N 0.000 claims 1
- MDJIPXYRSZHCFS-UHFFFAOYSA-N 2-phenyl-n-[5-[2-[2-[5-[(2-phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]ethylsulfanyl]ethyl]-1,3,4-thiadiazol-2-yl]acetamide Chemical compound N=1N=C(CCSCCC=2SC(NC(=O)CC=3C=CC=CC=3)=NN=2)SC=1NC(=O)CC1=CC=CC=C1 MDJIPXYRSZHCFS-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 108010024636 Glutathione Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000002231 Muscle Neoplasms Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 201000006491 bone marrow cancer Diseases 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229960003180 glutathione Drugs 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 238000011532 immunohistochemical staining Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000002077 muscle cancer Diseases 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762573906P | 2017-10-18 | 2017-10-18 | |
| US62/573,906 | 2017-10-18 | ||
| PCT/US2018/056567 WO2019079632A1 (en) | 2017-10-18 | 2018-10-18 | GLUTAMINASE INHIBITOR THERAPY |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021500335A JP2021500335A (ja) | 2021-01-07 |
| JP2021500335A5 true JP2021500335A5 (enExample) | 2021-11-25 |
| JP7361687B2 JP7361687B2 (ja) | 2023-10-16 |
Family
ID=66173506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020521600A Active JP7361687B2 (ja) | 2017-10-18 | 2018-10-18 | グルタミナーゼ阻害薬療法 |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US10722487B2 (enExample) |
| EP (1) | EP3697764B1 (enExample) |
| JP (1) | JP7361687B2 (enExample) |
| CN (1) | CN111225903B (enExample) |
| ES (1) | ES3040089T3 (enExample) |
| RU (1) | RU2020112558A (enExample) |
| WO (1) | WO2019079632A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3164394T1 (sl) | 2014-07-03 | 2020-08-31 | Board Of Regents, The University Of Texas System | GLS1 inhibitorji za zdravljenje bolezni |
| WO2017004359A1 (en) | 2015-06-30 | 2017-01-05 | Board Of Regents, University Of Texas System | Gls1 inhibitors for treating disease |
| CN108602782B (zh) | 2015-12-22 | 2022-06-17 | 德克萨斯大学系统董事会 | N-甲基-1h-1,2,3-三唑-4-甲酰胺化合物的盐形式和多晶型物 |
| CN111225903B (zh) | 2017-10-18 | 2024-08-16 | 德州大学系统董事会 | 谷氨酰胺酶抑制剂疗法 |
| US20250275964A1 (en) * | 2019-10-15 | 2025-09-04 | Cornell University | Methods of inhibiting liver-type glutaminase, gls2 |
| CN112791087B (zh) * | 2020-06-05 | 2023-06-30 | 厦门大学附属中山医院 | Bptes在制备预防或治疗炭疽病的药物中的用途 |
| CN117043153A (zh) * | 2020-12-11 | 2023-11-10 | 杭州紫晶医药科技有限公司 | 作为gls1抑制剂的杂环化合物 |
| JP2025078888A (ja) * | 2022-01-28 | 2025-05-21 | 国立大学法人富山大学 | グルタミナーゼ阻害剤 |
| KR102842785B1 (ko) * | 2022-09-07 | 2025-08-07 | 재단법인 아산사회복지재단 | 선행화학요법 내성의 고형암 환자 진단용 바이오마커 및 이를 이용한 선행화학요법 내성 진단을 위한 정보제공방법 |
| CN119326875A (zh) * | 2024-12-23 | 2025-01-21 | 中国人民解放军总医院第三医学中心 | L-ASNase在制备治疗膀胱癌药物中的应用及试剂盒 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES498337A0 (es) | 1980-01-07 | 1982-06-01 | Nyegaard & Co As | Un procedimiento para la preparacion de 5-halo-pirimidin-2- onas |
| EP0218753B1 (en) | 1985-10-10 | 1989-08-09 | Agfa-Gevaert N.V. | Image-recieving element for the silver salt diffusion transfer reversal process |
| WO1991009848A1 (en) | 1989-12-22 | 1991-07-11 | The Upjohn Company | Pyridinones useful as antiatherosclerotic agents |
| IL118325A0 (en) | 1995-05-25 | 1996-10-31 | Pont Merck And Pharmaceutical | Integrin receptor antagonists and pharmaceutical compositions containing them |
| WO1997003668A1 (en) | 1995-07-21 | 1997-02-06 | Constantia Gruppe | Treatment and prevention of neoplasms with salts of aminoimidazole carboxamide and 5-amino or substituted amino 1,2,3-triazoles |
| AU6780398A (en) | 1997-03-28 | 1998-10-22 | Du Pont Merck Pharmaceutical Company, The | Heterocyclic integrin inhibitor prodrugs |
| EP1049693A1 (en) | 1997-11-26 | 2000-11-08 | Du Pont Pharmaceuticals Company | 1,3,4-THIADIAZOLES AND 1,3,4-OXADIAZOLES AS $g(a) v?$g(b) 3? ANTAGONISTS |
| US6451828B1 (en) | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| NZ618298A (en) * | 2001-11-13 | 2015-04-24 | Univ Pennsylvania | A method of detecting and/or identifying adeno-associated virus (aav) sequences and isolating novel sequences identified thereby |
| SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| WO2007103290A2 (en) | 2006-03-03 | 2007-09-13 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Materials and methods directed to asparagine synthetase and asparaginase therapies |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| CA2686933A1 (en) | 2007-04-06 | 2008-10-16 | The Johns Hopkins University | Methods and compositions for the treatment of cancer |
| MX2010008198A (es) | 2008-02-25 | 2010-08-23 | Hoffmann La Roche | Inhibidores de cinasa de pirrolopirazina. |
| WO2009143389A1 (en) | 2008-05-21 | 2009-11-26 | Ariad Pharmaceuticals, Inc. | Phosphorous derivatives as kinase inhibitors |
| JP2011231015A (ja) | 2008-08-29 | 2011-11-17 | Taiho Yakuhin Kogyo Kk | 含窒素複素環を有する新規ウラシル化合物又はその塩 |
| CA2753382C (en) | 2009-02-27 | 2014-12-23 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| WO2010111504A2 (en) | 2009-03-25 | 2010-09-30 | Cornell University | Inhibition of glutaminase c |
| JP5725475B2 (ja) | 2010-01-21 | 2015-05-27 | 公立大学法人名古屋市立大学 | ヒドロキサム酸誘導体及びそれを用いたｈｄａｃ８阻害剤 |
| WO2011143160A2 (en) | 2010-05-10 | 2011-11-17 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| ES2761866T3 (es) | 2011-11-21 | 2020-05-21 | Calithera Biosciences Inc | Inhibidores heterocíclicos de glutaminasa |
| ES2899461T3 (es) | 2012-11-16 | 2022-03-11 | Calithera Biosciences Inc | Inhibidores heterocíclicos de glutaminasa |
| SG11201504022RA (en) | 2012-11-21 | 2015-06-29 | Agios Pharmaceuticals Inc | Glutamase inhibitors and method of use |
| WO2014079011A1 (en) | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| US9029531B2 (en) | 2012-11-22 | 2015-05-12 | Agios Pharmaceuticals, Inc. | Compounds and their methods of use |
| CN105283182A (zh) | 2012-12-03 | 2016-01-27 | 卡利泰拉生物科技公司 | 用谷氨酰胺酶的杂环抑制剂治疗癌症 |
| CN104955332B (zh) | 2013-01-30 | 2017-03-29 | 住友化学株式会社 | 防治节足害虫的方法 |
| TW201500356A (zh) | 2013-04-12 | 2015-01-01 | Lilly Co Eli | 二氫吡啶并嘧啶化合物 |
| CN111892589A (zh) | 2014-01-06 | 2020-11-06 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| WO2016004413A2 (en) | 2014-07-03 | 2016-01-07 | Board Of Regents, University Of Texas System | Gls1 inhibitors for treating disease |
| WO2016004418A1 (en) | 2014-07-03 | 2016-01-07 | Board Of Regents, University Of Texas System | Glutaminase inhibitor therapy |
| SI3164394T1 (sl) | 2014-07-03 | 2020-08-31 | Board Of Regents, The University Of Texas System | GLS1 inhibitorji za zdravljenje bolezni |
| US20160058759A1 (en) * | 2014-07-03 | 2016-03-03 | Board Of Regents, The University Of Texas System | Glutaminase inhibitor therapy |
| US20160002204A1 (en) | 2014-07-03 | 2016-01-07 | Board Of Regents, The University Of Texas System | Gls1 inhibitors for treating disease |
| WO2017004359A1 (en) | 2015-06-30 | 2017-01-05 | Board Of Regents, University Of Texas System | Gls1 inhibitors for treating disease |
| CN108602782B (zh) | 2015-12-22 | 2022-06-17 | 德克萨斯大学系统董事会 | N-甲基-1h-1,2,3-三唑-4-甲酰胺化合物的盐形式和多晶型物 |
| CN111225903B (zh) | 2017-10-18 | 2024-08-16 | 德州大学系统董事会 | 谷氨酰胺酶抑制剂疗法 |
-
2018
- 2018-10-18 CN CN201880067288.0A patent/CN111225903B/zh active Active
- 2018-10-18 US US16/164,581 patent/US10722487B2/en active Active
- 2018-10-18 EP EP18868394.0A patent/EP3697764B1/en active Active
- 2018-10-18 ES ES18868394T patent/ES3040089T3/es active Active
- 2018-10-18 WO PCT/US2018/056567 patent/WO2019079632A1/en not_active Ceased
- 2018-10-18 JP JP2020521600A patent/JP7361687B2/ja active Active
- 2018-10-18 RU RU2020112558A patent/RU2020112558A/ru unknown
-
2020
- 2020-06-03 US US16/891,791 patent/US11045443B2/en active Active
-
2021
- 2021-05-21 US US17/327,225 patent/US11786500B2/en active Active
-
2023
- 2023-09-06 US US18/461,724 patent/US12336976B2/en active Active
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