JP2015517557A5 - - Google Patents
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- Publication number
- JP2015517557A5 JP2015517557A5 JP2015513186A JP2015513186A JP2015517557A5 JP 2015517557 A5 JP2015517557 A5 JP 2015517557A5 JP 2015513186 A JP2015513186 A JP 2015513186A JP 2015513186 A JP2015513186 A JP 2015513186A JP 2015517557 A5 JP2015517557 A5 JP 2015517557A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- pyrrolidinyl
- piperidinyl
- methylsulfonyl
- 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 21
- -1 13 Chemical class 0.000 claims 14
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 101100327242 Drosophila melanogaster CycE gene Proteins 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 claims 3
- 101100059444 Mus musculus Ccnb1 gene Proteins 0.000 claims 3
- 101100112680 Ostreococcus tauri CycD gene Proteins 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 102100024170 Cyclin-C Human genes 0.000 claims 2
- 101000980770 Homo sapiens Cyclin-C Proteins 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- ZTVWUADOYUCSOA-QFRTYVPDSA-N (2s,4s)-1-[(e)-3-[5-chloro-2-(tetrazol-1-yl)phenyl]prop-2-enoyl]-4-[(3s)-3-methyl-4-sulfamoylpiperazin-1-yl]-n-phenylpyrrolidine-2-carboxamide Chemical compound C1CN(S(N)(=O)=O)[C@@H](C)CN1[C@@H]1CN(C(=O)\C=C\C=2C(=CC=C(Cl)C=2)N2N=NN=C2)[C@H](C(=O)NC=2C=CC=CC=2)C1 ZTVWUADOYUCSOA-QFRTYVPDSA-N 0.000 claims 1
- MOLPVSKHMAUZQO-ZXVVROJWSA-N (2s,4s)-4-[4-(benzenesulfonyl)piperazin-1-yl]-1-[(e)-3-[5-chloro-2-(tetrazol-1-yl)phenyl]prop-2-enoyl]-n-phenylpyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1C[C@@H](CN1C(=O)/C=C/C=1C(=CC=C(C=1)Cl)N1N=NN=C1)N1CCN(CC1)S(=O)(=O)C=1C=CC=CC=1)NC1=CC=CC=C1 MOLPVSKHMAUZQO-ZXVVROJWSA-N 0.000 claims 1
- KGAPLUOXQZIAGC-GWWGAPEBSA-N (2s,4s)-n-(2h-benzotriazol-5-yl)-1-[(e)-3-[5-chloro-2-(tetrazol-1-yl)phenyl]prop-2-enoyl]-4-morpholin-4-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H]2CN([C@@H](C2)C(=O)NC2=CC3=NNN=C3C=C2)C(=O)/C=C/C=2C(=CC=C(C=2)Cl)N2N=NN=C2)CCOCC1 KGAPLUOXQZIAGC-GWWGAPEBSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- WKLGVORXJYLGCX-MBSDFSHPSA-N 4-[[(2s,4r)-1-(3-chloro-4-fluoro-1-methylindole-5-carbonyl)-4-(1-methylsulfonylpiperidin-4-yl)pyrrolidine-2-carbonyl]amino]benzoic acid Chemical compound O=C([C@@H]1C[C@@H](CN1C(=O)C=1C(F)=C2C(Cl)=CN(C2=CC=1)C)C1CCN(CC1)S(C)(=O)=O)NC1=CC=C(C(O)=O)C=C1 WKLGVORXJYLGCX-MBSDFSHPSA-N 0.000 claims 1
- QRFYQKCKNQTQSA-PMACEKPBSA-N 4-[[(2s,4s)-1-(1-carbamimidoylpiperidine-4-carbonyl)-4-(4-methylsulfonylpiperazin-1-yl)pyrrolidine-2-carbonyl]amino]benzoic acid Chemical compound C1CN(S(=O)(=O)C)CCN1[C@@H]1CN(C(=O)C2CCN(CC2)C(N)=N)[C@H](C(=O)NC=2C=CC(=CC=2)C(O)=O)C1 QRFYQKCKNQTQSA-PMACEKPBSA-N 0.000 claims 1
- DCBBOIFLGAMQFC-SFTDATJTSA-N 4-[[(2s,4s)-1-(4-carbamimidoylbenzoyl)-4-(4-methylsulfonylpiperazin-1-yl)pyrrolidine-2-carbonyl]amino]benzoic acid Chemical compound C1CN(S(=O)(=O)C)CCN1[C@@H]1CN(C(=O)C=2C=CC(=CC=2)C(N)=N)[C@H](C(=O)NC=2C=CC(=CC=2)C(O)=O)C1 DCBBOIFLGAMQFC-SFTDATJTSA-N 0.000 claims 1
- XKCJWVCNDOVAHF-VAEGLNEYSA-N 4-[[(2s,4s)-1-[(e)-3-[5-chloro-2-(tetrazol-1-yl)phenyl]prop-2-enoyl]-4-morpholin-4-ylpyrrolidine-2-carbonyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)[C@H]1N(C(=O)\C=C\C=2C(=CC=C(Cl)C=2)N2N=NN=C2)C[C@@H](N2CCOCC2)C1 XKCJWVCNDOVAHF-VAEGLNEYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- KPHTWWMYMFXYAQ-MWYJAUPDSA-N NC[C@H]1CC[C@@H](CC1)C(=O)N1C[C@H](C[C@H]1C(=O)Nc1ccc(cc1)C(O)=O)N1CCN(CC1)S(=O)(=O)C1CC1 Chemical compound NC[C@H]1CC[C@@H](CC1)C(=O)N1C[C@H](C[C@H]1C(=O)Nc1ccc(cc1)C(O)=O)N1CCN(CC1)S(=O)(=O)C1CC1 KPHTWWMYMFXYAQ-MWYJAUPDSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 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 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CCCCCCCCCC(CC)*(*)N Chemical compound CCCCCCCCCC(CC)*(*)N 0.000 description 5
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1209138.5A GB201209138D0 (en) | 2012-05-24 | 2012-05-24 | Compounds |
| GB1209138.5 | 2012-05-24 | ||
| PCT/EP2013/060650 WO2013174937A1 (en) | 2012-05-24 | 2013-05-23 | Substituted pyrrolidines as factor xia inhibitors for the treatment thromboembolic diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017092396A Division JP6399148B2 (ja) | 2012-05-24 | 2017-05-08 | 血栓塞栓症の治療のための第ＸＩａ因子阻害剤としての置換ピロリジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517557A JP2015517557A (ja) | 2015-06-22 |
| JP2015517557A5 true JP2015517557A5 (enExample) | 2016-04-21 |
| JP6142919B2 JP6142919B2 (ja) | 2017-06-07 |
Family
ID=46546584
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015513186A Active JP6142919B2 (ja) | 2012-05-24 | 2013-05-23 | 血栓塞栓症の治療のための第ＸＩａ因子阻害剤としての置換ピロリジン |
| JP2017092396A Expired - Fee Related JP6399148B2 (ja) | 2012-05-24 | 2017-05-08 | 血栓塞栓症の治療のための第ＸＩａ因子阻害剤としての置換ピロリジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017092396A Expired - Fee Related JP6399148B2 (ja) | 2012-05-24 | 2017-05-08 | 血栓塞栓症の治療のための第ＸＩａ因子阻害剤としての置換ピロリジン |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US9394250B2 (enExample) |
| EP (2) | EP3056493B1 (enExample) |
| JP (2) | JP6142919B2 (enExample) |
| KR (1) | KR102090780B1 (enExample) |
| CN (1) | CN104379576B (enExample) |
| AU (1) | AU2013265256B2 (enExample) |
| BR (1) | BR112014027236A2 (enExample) |
| CA (1) | CA2874106C (enExample) |
| DK (1) | DK2855452T3 (enExample) |
| ES (2) | ES2628003T3 (enExample) |
| GB (1) | GB201209138D0 (enExample) |
| HU (1) | HUE034856T2 (enExample) |
| IL (1) | IL235767A (enExample) |
| MX (1) | MX363043B (enExample) |
| NZ (1) | NZ702070A (enExample) |
| PH (1) | PH12014502573B1 (enExample) |
| PL (1) | PL2855452T3 (enExample) |
| PT (1) | PT2855452T (enExample) |
| RU (1) | RU2636050C2 (enExample) |
| SG (1) | SG11201408271VA (enExample) |
| TW (1) | TWI573786B (enExample) |
| WO (1) | WO2013174937A1 (enExample) |
| ZA (1) | ZA201408593B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2534152B1 (en) | 2010-02-11 | 2018-05-02 | Bristol-Myers Squibb Company | Macrocycles as factor xia inhibitors |
| CN103974938B (zh) | 2011-10-14 | 2016-11-09 | 百时美施贵宝公司 | 作为因子xia抑制剂的经取代的四氢异喹啉化合物 |
| GB201209138D0 (en) * | 2012-05-24 | 2012-07-04 | Ono Pharmaceutical Co | Compounds |
| AU2013291098A1 (en) | 2012-07-19 | 2015-02-05 | Sumitomo Dainippon Pharma Co., Ltd. | 1-(cycloalkyl-carbonyl)proline derivative |
| US9409908B2 (en) | 2012-08-03 | 2016-08-09 | Bristol-Myers Squibb Company | Dihydropyridone p1 as factor XIa inhibitors |
| SG11201500270RA (en) | 2012-08-03 | 2015-03-30 | Bristol Myers Squibb Co | Dihydropyridone p1 as factor xia inhibitors |
| US9315519B2 (en) | 2012-10-12 | 2016-04-19 | Bristol-Myers Squibb Company | Guanidine substituted tetrahydroisoquinoline compounds as factor XIa inhibitors |
| JP6154473B2 (ja) | 2012-10-12 | 2017-06-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 第ＸＩａ因子阻害剤の結晶形 |
| WO2014059214A1 (en) | 2012-10-12 | 2014-04-17 | Bristol-Myers Squibb Company | Guanidine and amine substituted tetrahydroisoquinoline compounds as factor xia inhibitors |
| ES2712699T3 (es) | 2013-03-25 | 2019-05-14 | Bristol Myers Squibb Co | Tetrahidroisoquinolinas que contienen azoles sustituidos como inhibidores del factor XIa |
| JP6337750B2 (ja) * | 2013-11-22 | 2018-06-06 | 小野薬品工業株式会社 | 化合物 |
| CA2939326A1 (en) | 2014-01-14 | 2015-07-23 | Sumitomo Dainippon Pharma Co., Ltd. | Condensed 5-oxazolidinone derivative |
| TWI688564B (zh) | 2014-01-31 | 2020-03-21 | 美商必治妥美雅史谷比公司 | 作為凝血因子ｘｉａ抑制劑之具有雜環p2'基團之巨環化合物 |
| NO2760821T3 (enExample) | 2014-01-31 | 2018-03-10 | ||
| WO2016036893A1 (en) | 2014-09-04 | 2016-03-10 | Bristol-Myers Squibb Company | Diamide macrocycles that are fxia inhibitors |
| US9453018B2 (en) | 2014-10-01 | 2016-09-27 | Bristol-Myers Squibb Company | Pyrimidinones as factor XIa inhibitors |
| AR105646A1 (es) * | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| EP3371162B1 (en) | 2015-10-29 | 2022-01-26 | Merck Sharp & Dohme Corp. | Macrocyclic spirocarbamate derivatives as factor xia inhibitors, pharmaceutically acceptable compositions and their use |
| WO2017123518A1 (en) * | 2016-01-11 | 2017-07-20 | The Rockefeller University | Aminotriazole immunomodulators for treating autoimmune diseases |
| GB201608453D0 (en) * | 2016-05-13 | 2016-06-29 | Univ Liverpool | Muscle regeneration |
| WO2018039094A1 (en) | 2016-08-22 | 2018-03-01 | Merck Sharp & Dohme Corp. | Pyridine-1-oxide derivatives and their use as factor xia inhibitors |
| AU2018311976B2 (en) * | 2017-08-04 | 2022-10-13 | Takeda Pharmaceutical Company Limited | Inhibitors of Plasma Kallikrein and uses thereof |
| CN110240591A (zh) * | 2018-03-08 | 2019-09-17 | 天津药物研究院有限公司 | 脯氨酸衍生物及其制备方法和用途 |
| US20210371379A1 (en) * | 2018-09-20 | 2021-12-02 | Ono Pharmaceutical Co., Ltd. | Novel salt of 4-({(4s)-1-(4-carbamimidoylbenzoyl)-4-[4(methylsulfonyl)piperazin-1-yl]-l-prolyl}amino) benzoic acid and novel crystal form thereof |
| US11918570B2 (en) | 2020-04-13 | 2024-03-05 | The Research Foundation For The State University Of New York | Method of treatment for prevention of glucocorticoid toxicity and/or enhancement of muscle regeneration via neutrophil elastase inhibition |
| CN112915106A (zh) * | 2021-02-05 | 2021-06-08 | 张虎山 | 一种肿瘤免疫微环境调控剂的制备及其应用 |
| CN114507245B (zh) * | 2022-02-23 | 2024-03-19 | 江苏丽源医药有限公司 | 一种伊多塞班及其中间体的制备方法 |
| CN115010638B (zh) * | 2022-05-09 | 2024-02-13 | 杭州国瑞生物科技有限公司 | 一种奈玛特韦中间体的合成方法 |
| WO2025054361A1 (en) * | 2023-09-05 | 2025-03-13 | Apellis Pharmaceuticals, Inc. | Complement inhibition |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA951618B (en) | 1994-03-04 | 1996-08-27 | Lilly Co Eli | Antithrombotic agents |
| AU2002231235A1 (en) | 2000-11-07 | 2002-05-21 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| DE502004001289D1 (de) * | 2003-06-18 | 2006-10-05 | Merck Patent Gmbh | PYRROLIDIN-1,2-DICARBONSÄURE-1-i(4-ETHINYL-PHENYL)-AMIDö-2-i(PHENYL)-AMIDö DERIVATE ALS INHIBITOREN DER KOAGULATIONSFAKTOREN XA UND VIIA ZUR BEHANDLUNG VON THROMBOSEN |
| US7453002B2 (en) * | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| US7626039B2 (en) * | 2005-12-14 | 2009-12-01 | Bristol-Myers Squibb Company | Arylpropionamide, arylacrylamide, ayrlpropynamide, or arylmethylurea analogs as factor XIa inhibitors |
| ES2395538T3 (es) * | 2006-05-16 | 2013-02-13 | Boehringer Ingelheim International Gmbh | Prolinamidas sustituidas, su preparación y su uso como medicamentos |
| JP2009539873A (ja) * | 2006-06-08 | 2009-11-19 | ブリストル−マイヤーズ スクイブ カンパニー | 抗凝固剤として有用な第ＶＩＩａ因子インヒビターとしての２−アミノカルボニルフェニルアミノ−２−フェニルアセトアミド類 |
| EP2099778A2 (en) * | 2006-11-21 | 2009-09-16 | Smithkline Beecham Corporation | Amido anti-viral compounds |
| WO2008076805A2 (en) | 2006-12-15 | 2008-06-26 | Bristol-Myers Squibb Company | Arylpropionamide, arylacrylamide, arylpropynamide, or arylmethylurea analogs as factor xia inhibitors |
| CN101631784A (zh) * | 2006-12-20 | 2010-01-20 | 百时美施贵宝公司 | 用作抗凝血药的二环内酰胺凝血因子viia抑制剂 |
| AU2008266228A1 (en) * | 2007-06-13 | 2008-12-24 | Bristol-Myers Squibb Company | Dipeptide analogs as coagulation factor inhibitors |
| WO2009114677A1 (en) * | 2008-03-13 | 2009-09-17 | Bristol-Myers Squibb Company | Pyridazine derivatives as factor xia inhibitors |
| TW201011006A (en) * | 2008-06-16 | 2010-03-16 | Nuevolution As | IAP binding compounds |
| JP5580741B2 (ja) | 2008-09-19 | 2014-08-27 | 武田薬品工業株式会社 | 含窒素複素環化合物およびその用途 |
| CN102256944A (zh) | 2008-10-17 | 2011-11-23 | 埃克塞利希斯股份有限公司 | 鞘氨醇-1-磷酸受体拮抗剂 |
| GB201209138D0 (en) * | 2012-05-24 | 2012-07-04 | Ono Pharmaceutical Co | Compounds |
-
2012
- 2012-05-24 GB GBGB1209138.5A patent/GB201209138D0/en not_active Ceased
-
2013
- 2013-05-23 CA CA2874106A patent/CA2874106C/en not_active Expired - Fee Related
- 2013-05-23 SG SG11201408271VA patent/SG11201408271VA/en unknown
- 2013-05-23 DK DK13727822.2T patent/DK2855452T3/en active
- 2013-05-23 MX MX2014014246A patent/MX363043B/es unknown
- 2013-05-23 WO PCT/EP2013/060650 patent/WO2013174937A1/en not_active Ceased
- 2013-05-23 EP EP16159967.5A patent/EP3056493B1/en not_active Not-in-force
- 2013-05-23 TW TW102118195A patent/TWI573786B/zh not_active IP Right Cessation
- 2013-05-23 ES ES13727822.2T patent/ES2628003T3/es active Active
- 2013-05-23 AU AU2013265256A patent/AU2013265256B2/en not_active Ceased
- 2013-05-23 JP JP2015513186A patent/JP6142919B2/ja active Active
- 2013-05-23 BR BR112014027236A patent/BR112014027236A2/pt not_active Application Discontinuation
- 2013-05-23 PL PL13727822T patent/PL2855452T3/pl unknown
- 2013-05-23 RU RU2014152276A patent/RU2636050C2/ru active
- 2013-05-23 NZ NZ702070A patent/NZ702070A/en not_active IP Right Cessation
- 2013-05-23 ES ES16159967.5T patent/ES2637655T3/es active Active
- 2013-05-23 HU HUE13727822A patent/HUE034856T2/en unknown
- 2013-05-23 CN CN201380033214.2A patent/CN104379576B/zh not_active Expired - Fee Related
- 2013-05-23 US US14/403,037 patent/US9394250B2/en not_active Expired - Fee Related
- 2013-05-23 EP EP13727822.2A patent/EP2855452B1/en active Active
- 2013-05-23 PT PT137278222T patent/PT2855452T/pt unknown
- 2013-05-23 KR KR1020147031989A patent/KR102090780B1/ko not_active Expired - Fee Related
-
2014
- 2014-11-18 IL IL235767A patent/IL235767A/en active IP Right Grant
- 2014-11-19 PH PH12014502573A patent/PH12014502573B1/en unknown
- 2014-11-21 ZA ZA2014/08593A patent/ZA201408593B/en unknown
-
2016
- 2016-06-13 US US15/180,382 patent/US9585881B2/en not_active Expired - Fee Related
-
2017
- 2017-01-23 US US15/412,505 patent/US10336741B2/en not_active Expired - Fee Related
- 2017-05-08 JP JP2017092396A patent/JP6399148B2/ja not_active Expired - Fee Related
-
2019
- 2019-05-10 US US16/409,211 patent/US10882855B2/en not_active Expired - Fee Related
-
2020
- 2020-11-24 US US17/102,611 patent/US20210147403A1/en not_active Abandoned
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