JP2014513046A5 - - Google Patents
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- Publication number
- JP2014513046A5 JP2014513046A5 JP2013553647A JP2013553647A JP2014513046A5 JP 2014513046 A5 JP2014513046 A5 JP 2014513046A5 JP 2013553647 A JP2013553647 A JP 2013553647A JP 2013553647 A JP2013553647 A JP 2013553647A JP 2014513046 A5 JP2014513046 A5 JP 2014513046A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterium
- alkyl
- cycloalkyl
- compound
- phenyl
- 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.)
- Pending
Links
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 45
- 229910052805 deuterium Inorganic materials 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 201000003631 narcolepsy Diseases 0.000 claims description 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 230000000422 nocturnal effect Effects 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 208000001640 Fibromyalgia Diseases 0.000 claims description 6
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 6
- VWYANPOOORUCFJ-UHFFFAOYSA-N alpha-Fernenol Chemical compound CC1(C)C(O)CCC2(C)C3=CCC4(C)C5CCC(C(C)C)C5(C)CCC4(C)C3CCC21 VWYANPOOORUCFJ-UHFFFAOYSA-N 0.000 claims description 6
- 206010022437 insomnia Diseases 0.000 claims description 6
- 229960003928 sodium oxybate Drugs 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 claims description 4
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical group C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims description 4
- 108090000312 Calcium Channels Proteins 0.000 claims description 4
- 102000003922 Calcium Channels Human genes 0.000 claims description 4
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims description 4
- 230000005856 abnormality Effects 0.000 claims description 4
- 230000009977 dual effect Effects 0.000 claims description 4
- 229960002866 duloxetine Drugs 0.000 claims description 4
- 229960002870 gabapentin Drugs 0.000 claims description 4
- 229960000600 milnacipran Drugs 0.000 claims description 4
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 4
- 229960001233 pregabalin Drugs 0.000 claims description 4
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 claims description 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960004688 venlafaxine Drugs 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 3
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 208000004547 Hallucinations Diseases 0.000 claims description 3
- 206010019468 Hemiplegia Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010039897 Sedation Diseases 0.000 claims description 3
- 208000005439 Sleep paralysis Diseases 0.000 claims description 3
- 208000032140 Sleepiness Diseases 0.000 claims description 3
- 206010041349 Somnolence Diseases 0.000 claims description 3
- 201000007930 alcohol dependence Diseases 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 201000006517 essential tremor Diseases 0.000 claims description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 3
- 208000001797 obstructive sleep apnea Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000036280 sedation Effects 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000022925 sleep disturbance Diseases 0.000 claims description 3
- 230000037321 sleepiness Effects 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002510 pyrogen Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000000946 synaptic effect Effects 0.000 description 3
- 208000019505 Deglutition disease Diseases 0.000 description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical class OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161442451P | 2011-02-14 | 2011-02-14 | |
| US61/442,451 | 2011-02-14 | ||
| US201161484296P | 2011-05-10 | 2011-05-10 | |
| US61/484,296 | 2011-05-10 | ||
| PCT/US2012/024974 WO2012112492A1 (en) | 2011-02-14 | 2012-02-14 | 4-hydroxybutyric acid deuterated analogs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083295A Division JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014513046A JP2014513046A (ja) | 2014-05-29 |
| JP2014513046A5 true JP2014513046A5 (cg-RX-API-DMAC7.html) | 2015-04-02 |
Family
ID=46672903
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013553647A Pending JP2014513046A (ja) | 2011-02-14 | 2012-02-14 | ４−ヒドロキシ酪酸の重水素化類似体 |
| JP2017083295A Active JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083295A Active JP6692319B2 (ja) | 2011-02-14 | 2017-04-20 | ４−ヒドロキシ酪酸の重水素化類似体 |
Country Status (10)
| Country | Link |
|---|---|
| US (5) | US8759394B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2675771B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2014513046A (cg-RX-API-DMAC7.html) |
| KR (1) | KR101976218B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN103370289B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112013020620A2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2804540T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL227754B (cg-RX-API-DMAC7.html) |
| MX (1) | MX355742B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012112492A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2421808T1 (sl) | 2009-04-23 | 2013-12-31 | Concert Pharmaceuticals Inc. | Analogi 4-hidroksi maslene kisline |
| BR112012024019B1 (pt) | 2010-03-24 | 2021-10-19 | Jazz Phamaceuticals, Inc | Forma de dosagem de liberação controlada para administração oral |
| MX355742B (es) * | 2011-02-14 | 2018-04-26 | Concert Pharmaceuticals Inc | Análogos deuterados del ácido 4-hidroxibutírico. |
| US10398662B1 (en) | 2015-02-18 | 2019-09-03 | Jazz Pharma Ireland Limited | GHB formulation and method for its manufacture |
| CA3207643A1 (en) | 2015-09-23 | 2017-03-30 | XWPharma Ltd. | Prodrugs of gamma-hydroxybutyric acid, compositions and uses thereof |
| WO2017086447A1 (ja) * | 2015-11-19 | 2017-05-26 | 協和発酵バイオ株式会社 | ３－ヒドロキシイソ吉草酸の一価カチオン塩の結晶および該結晶の製造方法 |
| AU2017282515A1 (en) | 2016-06-24 | 2019-01-17 | Otsuka Pharmaceutical Factory, Inc. | Crystal of β-hydroxy β-methylbutyric acid amino acid salt and production method therefor |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11000498B2 (en) | 2016-07-22 | 2021-05-11 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US20180263936A1 (en) | 2017-03-17 | 2018-09-20 | Jazz Pharmaceuticals Ireland Limited | Gamma-hydroxybutyrate compositions and their use for the treatment of disorders |
| BR112019020464A2 (pt) | 2017-03-30 | 2020-04-28 | Xw Laboratories Inc. | compostos derivados de heteroarila bicíclica, composição farmacêutica compreendendo os ditos compostos, adesivo transdérmico compreendendo a dita composição e uso terapêutico dos compostos e composição |
| CA3093430A1 (en) * | 2018-03-23 | 2019-09-26 | Concert Pharmaceuticals, Inc. | Deuterated analogs of d-.beta.-hydroxybutyric acid and uses thereof |
| ES2947089T3 (es) | 2018-09-30 | 2023-08-01 | Xwpharma Ltd | Compuestos como antagonistas del receptor histamínico 3 neuronal y usos de los mismos |
| US11400052B2 (en) | 2018-11-19 | 2022-08-02 | Jazz Pharmaceuticals Ireland Limited | Alcohol-resistant drug formulations |
| AU2020231916B2 (en) | 2019-03-01 | 2025-08-28 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| WO2021127461A1 (en) | 2019-12-20 | 2021-06-24 | Xw Laboratories Limited | Methods of synthesizing 4-valyloxybutyric acid |
| TW202139986A (zh) | 2020-02-21 | 2021-11-01 | 愛爾蘭商爵士製藥愛爾蘭有限責任公司 | 治療原發性嗜睡症之方法 |
| AU2021292406B2 (en) | 2020-06-18 | 2024-03-14 | XWPharma Ltd. | Controlled release granulations of water-soluble active pharmaceutical ingredients |
| KR20230008190A (ko) | 2020-06-18 | 2023-01-13 | 엑스더블유파마 리미티드 | 수용성 원료의약품의 약학적 과립화제 |
| WO2022020621A1 (en) | 2020-07-24 | 2022-01-27 | XWPharma Ltd. | Pharmaceutical compositions and pharmacokinetics of a gamma-hydroxybutyric acid derivative |
| AU2021357705B2 (en) | 2020-10-05 | 2024-09-26 | XWPharma Ltd. | Modified release compositions of a gamma-hydroxybutyric acid derivative |
| EP4308086B1 (en) | 2021-03-19 | 2025-10-15 | XWPharma Ltd. | Pharmacokinetics of combined release formulations of a gamma-hydroxybutyric acid derivative |
| CN113200853A (zh) * | 2021-05-19 | 2021-08-03 | 宁波窦氏化学科技有限公司 | 一种制备丁二酸二醇酯的工艺方法 |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| WO2025137671A1 (en) * | 2023-12-22 | 2025-06-26 | Temple University-Of The Commonwealth System Of Higher Education | Short chain fatty acid compounds and uses thereof |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA814854B (en) * | 1980-07-17 | 1982-07-28 | J Klosa | Nonhygroscopic salts of 4-hydroxybutryric acid, methods of their production and pharmaceutical preparations containing these salts |
| EP0044801B1 (de) | 1980-07-17 | 1984-02-15 | Josef Dr. Klosa | Nichthygroskopische Salze der 4-Hydroxybuttersäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Mittel |
| US4548716A (en) * | 1984-07-25 | 1985-10-22 | Lucas Boeve | Method of producing ultrapure, pyrogen-free water |
| US4738985A (en) | 1986-03-19 | 1988-04-19 | The University Of Toronto Innovations Foundations | Pharmaceutical composition and treatment |
| JP2727008B2 (ja) * | 1989-02-01 | 1998-03-11 | 日本酸素株式会社 | 静菌化水の製造方法 |
| DE4113984C2 (de) | 1991-04-29 | 2002-05-08 | Koehler Chemie Dr Franz | Salze der 4-Hydroxy-Buttersäure |
| IT1248588B (it) * | 1991-06-28 | 1995-01-19 | Gaetano Crepaldi | Composizioni farmaceutiche per la terapia dell'astinenza, del " craving", della dipendenza da sostanze stupefacenti, da sostanze psicoattive, da nicotina e dei disturbi alimentari. |
| AU707748B2 (en) | 1994-03-25 | 1999-07-22 | Isotechnika Inc. | Enhancement of the efficacy of drugs by deuteration |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| US5840331A (en) | 1995-06-07 | 1998-11-24 | Arch Development Corporation | Use of γ-hydroxybutyrate for the stimulation of sleep-related secretion growth hormone and prolactin |
| AU749638B2 (en) * | 1997-03-17 | 2002-06-27 | Btg International Limited | Therapeutic compositions |
| US5990162A (en) | 1997-08-29 | 1999-11-23 | Orphan Medical, Inc. | Method for treatment of fibromyalgia and chronic fatigue syndrome |
| US6440710B1 (en) | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| ES2240163T3 (es) | 1999-09-14 | 2005-10-16 | Tepha, Inc. | Utilizaciones terapeuticas de polimeros y de oligomeros a base de gamma-hidroxibutirano (ghb). |
| US6204245B1 (en) | 1999-09-17 | 2001-03-20 | The Regents Of The University Of California | Treatment of narcolepsy with immunosuppressants |
| EP1104760B1 (en) | 1999-12-03 | 2003-03-12 | Pfizer Products Inc. | Sulfamoylheteroaryl pyrazole compounds as anti-inflammatory/analgesic agents |
| CA2423358C (en) | 2000-09-22 | 2011-05-17 | Orphan Medical, Inc. | Gamma-hydroxybutyrate compositions containing carbohydrate, lipid or amino acid carriers |
| US7727549B2 (en) | 2002-07-15 | 2010-06-01 | Alcon, Inc. | Pharmaceutical compositions for otic use |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| CN101309917B (zh) | 2005-10-06 | 2013-09-11 | 奥斯拜客斯制药有限公司 | 具有增强治疗性质的胃h+，k+-atp酶氘代抑制剂 |
| US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| WO2008030382A1 (en) | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| US20090082380A1 (en) * | 2007-09-25 | 2009-03-26 | Protia, Llc | Deuterium-enriched rosuvastatin |
| KR101810246B1 (ko) * | 2008-10-08 | 2017-12-18 | 엑스진 파마슈티컬 인크. | Ｇａｂａ 접합체 및 그의 사용 방법 |
| SI2421808T1 (sl) | 2009-04-23 | 2013-12-31 | Concert Pharmaceuticals Inc. | Analogi 4-hidroksi maslene kisline |
| MX355742B (es) * | 2011-02-14 | 2018-04-26 | Concert Pharmaceuticals Inc | Análogos deuterados del ácido 4-hidroxibutírico. |
-
2012
- 2012-02-14 MX MX2013009368A patent/MX355742B/es active IP Right Grant
- 2012-02-14 US US13/372,989 patent/US8759394B2/en active Active
- 2012-02-14 JP JP2013553647A patent/JP2014513046A/ja active Pending
- 2012-02-14 EP EP12704646.4A patent/EP2675771B1/en active Active
- 2012-02-14 BR BR112013020620A patent/BR112013020620A2/pt not_active Application Discontinuation
- 2012-02-14 KR KR1020137024419A patent/KR101976218B1/ko active Active
- 2012-02-14 ES ES12704646T patent/ES2804540T3/es active Active
- 2012-02-14 CN CN201280008737.7A patent/CN103370289B/zh active Active
- 2012-02-14 WO PCT/US2012/024974 patent/WO2012112492A1/en not_active Ceased
-
2013
- 2013-08-01 IL IL227754A patent/IL227754B/en active IP Right Grant
-
2014
- 2014-04-17 US US14/255,331 patent/US9309182B2/en active Active
-
2016
- 2016-04-11 US US15/095,545 patent/US10040748B2/en active Active
-
2017
- 2017-04-20 JP JP2017083295A patent/JP6692319B2/ja active Active
-
2018
- 2018-08-06 US US16/055,407 patent/US20190100484A1/en not_active Abandoned
-
2021
- 2021-02-01 US US17/164,391 patent/US20210403407A1/en not_active Abandoned
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