JP2016505512A5 - - Google Patents
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- Publication number
- JP2016505512A5 JP2016505512A5 JP2015539801A JP2015539801A JP2016505512A5 JP 2016505512 A5 JP2016505512 A5 JP 2016505512A5 JP 2015539801 A JP2015539801 A JP 2015539801A JP 2015539801 A JP2015539801 A JP 2015539801A JP 2016505512 A5 JP2016505512 A5 JP 2016505512A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- lower alkyl
- pde4
- cyano
- 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
- 150000001875 compounds Chemical class 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 18
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 18
- -1 trifluoromethoxy, hydroxyl Chemical group 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 230000001404 mediated effect Effects 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- XOQABDOICLHPIS-UHFFFAOYSA-N 1-hydroxy-2,1-benzoxaborole Chemical compound C1=CC=C2B(O)OCC2=C1 XOQABDOICLHPIS-UHFFFAOYSA-N 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 6
- 101000988424 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4B Proteins 0.000 claims 6
- 101000988419 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4D Proteins 0.000 claims 6
- 102100029168 cAMP-specific 3',5'-cyclic phosphodiesterase 4B Human genes 0.000 claims 6
- 102100029170 cAMP-specific 3',5'-cyclic phosphodiesterase 4D Human genes 0.000 claims 6
- 230000006870 function Effects 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 230000003920 cognitive function Effects 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261718285P | 2012-10-25 | 2012-10-25 | |
| US61/718,285 | 2012-10-25 | ||
| US201261733675P | 2012-12-05 | 2012-12-05 | |
| US61/733,675 | 2012-12-05 | ||
| US201361776937P | 2013-03-12 | 2013-03-12 | |
| US61/776,937 | 2013-03-12 | ||
| PCT/US2013/066645 WO2014066659A1 (en) | 2012-10-25 | 2013-10-24 | Heteroaryl inhibitors of pde4 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505512A JP2016505512A (ja) | 2016-02-25 |
| JP2016505512A5 true JP2016505512A5 (OSRAM) | 2016-12-15 |
| JP6289485B2 JP6289485B2 (ja) | 2018-03-07 |
Family
ID=50545269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015539801A Active JP6289485B2 (ja) | 2012-10-25 | 2013-10-24 | Ｐｄｅ４のヘテロアリール阻害剤 |
Country Status (22)
| Country | Link |
|---|---|
| US (8) | US9221843B2 (OSRAM) |
| EP (2) | EP3842420B1 (OSRAM) |
| JP (1) | JP6289485B2 (OSRAM) |
| KR (1) | KR102189560B1 (OSRAM) |
| CN (1) | CN104768932B (OSRAM) |
| AU (1) | AU2013334236B2 (OSRAM) |
| BR (1) | BR112015009168B1 (OSRAM) |
| CA (1) | CA2886263C (OSRAM) |
| CL (1) | CL2015001068A1 (OSRAM) |
| DK (1) | DK2912019T3 (OSRAM) |
| ES (1) | ES2871821T3 (OSRAM) |
| HR (1) | HRP20230162T1 (OSRAM) |
| HU (1) | HUE056251T2 (OSRAM) |
| IL (1) | IL238409A (OSRAM) |
| LT (1) | LT3842420T (OSRAM) |
| MX (1) | MX368959B (OSRAM) |
| NZ (1) | NZ705881A (OSRAM) |
| PL (1) | PL2912019T3 (OSRAM) |
| PT (1) | PT2912019T (OSRAM) |
| SG (1) | SG11201502050XA (OSRAM) |
| SI (1) | SI3842420T1 (OSRAM) |
| WO (1) | WO2014066659A1 (OSRAM) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2861566T (pt) | 2012-06-13 | 2017-02-08 | Hoffmann La Roche | Novos diazaspirocicloalcanos e azaspirocicloalcanos |
| AU2013322838B2 (en) | 2012-09-25 | 2018-02-01 | F. Hoffmann-La Roche Ag | New bicyclic derivatives |
| WO2014066659A1 (en) | 2012-10-25 | 2014-05-01 | Tetra Discovery Partners, Llc. | Heteroaryl inhibitors of pde4 |
| JP6307524B2 (ja) | 2013-02-04 | 2018-04-04 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Ｐｄｅ４阻害薬としての、４−アミノ置換縮合ピリミジン化合物 |
| EP2951173B1 (en) * | 2013-02-04 | 2017-05-17 | Grünenthal GmbH | Novel substituted condensed pyrimidine compounds |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| AU2014356583B2 (en) | 2013-11-26 | 2019-02-28 | F. Hoffmann-La Roche Ag | New octahydro-cyclobuta (1,2-c;3,4-c')dipyrrol-2-yl |
| AU2015238537B2 (en) | 2014-03-26 | 2019-08-01 | F. Hoffmann-La Roche Ag | Bicyclic compounds as autotaxin (ATX) and lysophosphatidic acid (LPA) production inhibitors |
| WO2015144609A1 (en) | 2014-03-26 | 2015-10-01 | F. Hoffmann-La Roche Ag | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| WO2016161268A1 (en) | 2015-04-01 | 2016-10-06 | Enanta Pharmaceuticals, Inc. | Hepatitis b antviral agents |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| US10738035B2 (en) | 2015-05-13 | 2020-08-11 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| WO2017011552A1 (en) | 2015-07-13 | 2017-01-19 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| US10301255B2 (en) | 2015-07-22 | 2019-05-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| UA123362C2 (uk) | 2015-09-04 | 2021-03-24 | Ф. Хоффманн-Ля Рош Аг | Феноксиметильні похідні |
| AU2016328535A1 (en) | 2015-09-24 | 2017-11-09 | F. Hoffmann-La Roche Ag | Bicyclic compounds as ATX inhibitors |
| CR20180072A (es) | 2015-09-24 | 2018-02-26 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores de atx |
| KR20180053408A (ko) | 2015-09-24 | 2018-05-21 | 에프. 호프만-라 로슈 아게 | 이중 오토탁신(atx)/탄산 무수화효소(ca) 억제제로서의 신규한 이환형 화합물 |
| CR20180057A (es) | 2015-09-24 | 2018-04-02 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de atx/ca. |
| WO2017136403A1 (en) | 2016-02-02 | 2017-08-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| MX384836B (es) | 2016-03-07 | 2025-03-14 | Enanta Pharm Inc | Agentes antivirales contra la hepatitis b |
| KR20190027814A (ko) * | 2016-06-10 | 2019-03-15 | 이난타 파마슈티칼스, 인코포레이티드 | B형 간염 항바이러스제 |
| CN110382484B (zh) | 2017-03-16 | 2022-12-06 | 豪夫迈·罗氏有限公司 | 新的作为atx抑制剂的二环化合物 |
| SG11201908560SA (en) | 2017-03-16 | 2019-10-30 | Hoffmann La Roche | Heterocyclic compounds useful as dual atx/ca inhibitors |
| NZ762994A (en) | 2017-08-28 | 2025-11-28 | Enanta Pharm Inc | Hepatitis b antiviral agents |
| JP7216719B2 (ja) | 2017-09-20 | 2023-02-01 | ユニオン・セラピューティクス・アクティエセルスカブ | 置換ジヒドロチエノピリミジンおよびホスホジエステラーゼ阻害剤としてのその使用 |
| WO2019113173A1 (en) | 2017-12-06 | 2019-06-13 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| US10723733B2 (en) | 2017-12-06 | 2020-07-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| CN111712502B (zh) | 2017-12-15 | 2023-10-27 | 联合疗法公司 | 取代的氮杂环丁烷二氢噻吩并嘧啶类化合物及其作为磷酸二酯酶抑制剂的用途 |
| CN111727191B (zh) * | 2017-12-15 | 2024-01-05 | 联合疗法公司 | 取代的氮杂环丁烷二氢噻吩并吡啶类化合物及其作为磷酸二酯酶抑制剂的用途 |
| US11058678B2 (en) | 2018-01-22 | 2021-07-13 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| WO2019191166A1 (en) | 2018-03-29 | 2019-10-03 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2019193091A1 (en) | 2018-04-05 | 2019-10-10 | Universiteit Hasselt | Selective pde4d inhibitors against demyelinating diseases |
| CN108997394A (zh) * | 2018-06-12 | 2018-12-14 | 广州百霆医药科技有限公司 | 苯并氧杂硼杂环戊烷类化合物及其制备方法 |
| AR116474A1 (es) | 2018-09-21 | 2021-05-12 | Enanta Pharm Inc | DERIVADOS DEL ÁCIDO 6,7-DIHIDRO-2H-BENZOFURO[2,3-a]QUINOLIZIN-3-CARBOXÍLICO COMO AGENTES ANTIVIRALES PARA EL TRATAMIENTO O PREVENCIÓN DE UNA INFECCIÓN POR HBV |
| SG11202102674RA (en) * | 2018-10-05 | 2021-04-29 | Pfizer | Boron containing pde4 inhibitors |
| SG11202105007TA (en) | 2018-11-21 | 2021-06-29 | Enanta Pharm Inc | Functionalized heterocycles as antiviral agents |
| CN111635400A (zh) | 2019-03-02 | 2020-09-08 | 察略盛医药科技(上海)有限公司 | 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 |
| WO2020214874A1 (en) * | 2019-04-18 | 2020-10-22 | Tetra Discovery Partners, Inc. | Salts and polymorphs of a pde4 inhibitor |
| WO2020232470A1 (en) | 2019-05-13 | 2020-11-19 | Boragen, Inc. | Chemical compounds |
| US11236111B2 (en) | 2019-06-03 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| US11760755B2 (en) | 2019-06-04 | 2023-09-19 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| WO2020247575A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| CN114341145B (zh) * | 2019-07-03 | 2024-08-16 | 博拉公司 | 化学化合物 |
| WO2021007488A1 (en) | 2019-07-11 | 2021-01-14 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| WO2021055425A2 (en) | 2019-09-17 | 2021-03-25 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| WO2021188414A1 (en) | 2020-03-16 | 2021-09-23 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
| CN114149410B (zh) * | 2020-09-07 | 2025-02-25 | 四川科伦博泰生物医药股份有限公司 | 吡啶并环类化合物及其制备方法和用途 |
| US20240116856A1 (en) * | 2020-11-05 | 2024-04-11 | Young Biopharma, Llc | Novel capsaicin analogs and uses thereof |
| CN116133666A (zh) * | 2020-12-25 | 2023-05-16 | 瑞石生物医药有限公司 | 一种硼酸酯衍生物及其用途 |
| CN115521946B (zh) * | 2022-10-14 | 2024-06-21 | 浙江玖世生物科技有限公司 | 一种TiOx基光酶催化剂合成(R)-1-[3,5-二(三氟甲基)]苯乙醇的方法 |
| EP4640219A1 (en) * | 2022-12-23 | 2025-10-29 | Shionogi & Co., Ltd. | Capsule or granules containing pde4 inhibitor |
| CN118871444A (zh) * | 2023-02-28 | 2024-10-29 | 上海翊石医药科技有限公司 | 二氢噻吩并嘧啶衍生物的制备方法和用途 |
| GB202306663D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Combination therapy |
| US20250120957A1 (en) | 2023-10-12 | 2025-04-17 | Alto Neuroscience, Inc. | Treatment of neuropsychiatric disorders with tilivapram |
| WO2025161532A1 (zh) * | 2024-02-01 | 2025-08-07 | 艾派克斯生物科技有限公司 | Pde4b抑制剂及其药物组合物和用途 |
| WO2025221488A1 (en) | 2024-04-16 | 2025-10-23 | Alto Neuroscience, Inc. | Transdermal administration of pde4 inhibitors for reduction in adverse events |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK23392D0 (da) | 1992-02-24 | 1992-02-24 | Novo Nordisk As | Heterocykliske forbindelser, deres anvendelse og fremstilling |
| FR2754260B1 (fr) | 1996-10-04 | 1998-10-30 | Adir | Nouveaux derives substitues de biphenyle ou de phenylpyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2000015645A1 (fr) * | 1998-09-11 | 2000-03-23 | Kyorin Pharmaceutical Co., Ltd. | Derives d'esters phosphoniques et leur procede de production |
| MXPA04008671A (es) | 2002-03-08 | 2004-12-06 | Lilly Co Eli | Derivados de pirrol-2,5-diona y su uso como inhibidores de gsk-3. |
| US20050014767A1 (en) | 2003-01-29 | 2005-01-20 | Magnus Pfahl | Benzoxazole, benzothiazole, and benzimidazole derivatives for the treatment of cancer and other diseases |
| JP2006123639A (ja) | 2004-10-27 | 2006-05-18 | Mitsubishi Electric Corp | ホームドア状態認識システム |
| US20060293343A1 (en) * | 2005-05-18 | 2006-12-28 | Asahi Kasei Pharma Corporation | Pyrimidine derivatives |
| WO2006123639A1 (ja) * | 2005-05-18 | 2006-11-23 | Asahi Kasei Pharma Corporation | ピリミジン誘導体 |
| US7919519B2 (en) | 2005-11-23 | 2011-04-05 | Epix Pharmaceuticals Inc. | S1P receptor modulating compounds and use thereof |
| WO2009146388A1 (en) | 2008-05-28 | 2009-12-03 | The Trustees Of Columbia University In The City Of New York | Voxel-based methods for assessing subjects using positron emission tomography |
| WO2010027975A1 (en) * | 2008-09-04 | 2010-03-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| RU2380890C1 (ru) | 2008-10-17 | 2010-02-10 | Государственное образовательное учреждение высшего профессионального образования Марийский государственный технический университет | Способ испытания травяного покрова на прирусловой пойме реки |
| WO2010059838A2 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects |
| EP2400962B1 (de) * | 2009-02-27 | 2017-11-08 | Boehringer Ingelheim International GmbH | Arzneimittelkombinationen enthaltend pde4-inhibitoren und nsaids |
| EP2380890A1 (en) * | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
| US8889123B2 (en) * | 2010-08-19 | 2014-11-18 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| WO2014066659A1 (en) | 2012-10-25 | 2014-05-01 | Tetra Discovery Partners, Llc. | Heteroaryl inhibitors of pde4 |
| EP2951173B1 (en) * | 2013-02-04 | 2017-05-17 | Grünenthal GmbH | Novel substituted condensed pyrimidine compounds |
| US20150086480A1 (en) | 2013-09-26 | 2015-03-26 | Tetra Discovery Partners, LLC | Heteroaryl inhibitors of pde4 |
| WO2016049595A1 (en) | 2014-09-26 | 2016-03-31 | Tetra Discovery Partners, LLC | Heteroaryl inhibitors of pde4 |
| WO2020214874A1 (en) * | 2019-04-18 | 2020-10-22 | Tetra Discovery Partners, Inc. | Salts and polymorphs of a pde4 inhibitor |
-
2013
- 2013-10-24 WO PCT/US2013/066645 patent/WO2014066659A1/en not_active Ceased
- 2013-10-24 MX MX2015005015A patent/MX368959B/es active IP Right Grant
- 2013-10-24 SI SI201332034T patent/SI3842420T1/sl unknown
- 2013-10-24 PL PL13848739T patent/PL2912019T3/pl unknown
- 2013-10-24 CA CA2886263A patent/CA2886263C/en active Active
- 2013-10-24 US US14/349,688 patent/US9221843B2/en active Active
- 2013-10-24 BR BR112015009168-7A patent/BR112015009168B1/pt active IP Right Grant
- 2013-10-24 HU HUE13848739A patent/HUE056251T2/hu unknown
- 2013-10-24 JP JP2015539801A patent/JP6289485B2/ja active Active
- 2013-10-24 LT LTEP21156065.1T patent/LT3842420T/lt unknown
- 2013-10-24 PT PT138487392T patent/PT2912019T/pt unknown
- 2013-10-24 KR KR1020157010502A patent/KR102189560B1/ko active Active
- 2013-10-24 EP EP21156065.1A patent/EP3842420B1/en active Active
- 2013-10-24 DK DK13848739.2T patent/DK2912019T3/da active
- 2013-10-24 ES ES13848739T patent/ES2871821T3/es active Active
- 2013-10-24 CN CN201380055959.9A patent/CN104768932B/zh active Active
- 2013-10-24 EP EP13848739.2A patent/EP2912019B1/en active Active
- 2013-10-24 HR HRP20230162TT patent/HRP20230162T1/hr unknown
- 2013-10-24 NZ NZ705881A patent/NZ705881A/en unknown
- 2013-10-24 SG SG11201502050XA patent/SG11201502050XA/en unknown
- 2013-10-24 AU AU2013334236A patent/AU2013334236B2/en active Active
-
2015
- 2015-04-21 IL IL238409A patent/IL238409A/en active IP Right Grant
- 2015-04-24 CL CL2015001068A patent/CL2015001068A1/es unknown
- 2015-11-11 US US14/938,544 patent/US9777024B2/en active Active
-
2017
- 2017-08-18 US US15/680,842 patent/US10093686B2/en active Active
-
2018
- 2018-08-24 US US16/111,700 patent/US10364258B2/en active Active
-
2019
- 2019-04-26 US US16/396,457 patent/US10626129B2/en active Active
-
2020
- 2020-02-04 US US16/781,748 patent/US11401286B2/en active Active
-
2022
- 2022-06-23 US US17/808,439 patent/US11767334B2/en active Active
-
2023
- 2023-07-11 US US18/350,452 patent/US12264169B2/en active Active
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