JP2019537624A5 - - Google Patents
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- Publication number
- JP2019537624A5 JP2019537624A5 JP2019542758A JP2019542758A JP2019537624A5 JP 2019537624 A5 JP2019537624 A5 JP 2019537624A5 JP 2019542758 A JP2019542758 A JP 2019542758A JP 2019542758 A JP2019542758 A JP 2019542758A JP 2019537624 A5 JP2019537624 A5 JP 2019537624A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- benzimidazol
- ethyl
- methoxy
- 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 138
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- -1 carboxylic acid halides Chemical class 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 8
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000012351 deprotecting agent Substances 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 208000020016 psychiatric disease Diseases 0.000 claims description 8
- 208000019116 sleep disease Diseases 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 claims description 6
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- REFADFWJUIEDOA-UHFFFAOYSA-N N-[1-(2-ethoxy-6-methoxybenzimidazol-1-yl)propan-2-yl]acetamide Chemical compound C(C)(=O)NC(CN1C(=NC2=C1C=C(C=C2)OC)OCC)C REFADFWJUIEDOA-UHFFFAOYSA-N 0.000 claims description 2
- OSKMTHQTYBZVLY-UHFFFAOYSA-N N-[2-(2,6-dimethoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OC OSKMTHQTYBZVLY-UHFFFAOYSA-N 0.000 claims description 2
- FYOPITGSWFKTOI-UHFFFAOYSA-N N-[2-(2,6-dimethoxybenzimidazol-1-yl)ethyl]butanamide Chemical compound COC1=NC2=C(N1CCNC(CCC)=O)C=C(C=C2)OC FYOPITGSWFKTOI-UHFFFAOYSA-N 0.000 claims description 2
- ISXMRHJAUNQJBR-UHFFFAOYSA-N N-[2-(2,6-dimethoxybenzimidazol-1-yl)ethyl]propanamide Chemical compound COC1=NC2=C(N1CCNC(CC)=O)C=C(C=C2)OC ISXMRHJAUNQJBR-UHFFFAOYSA-N 0.000 claims description 2
- MRWHUOOPUIAFSB-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC MRWHUOOPUIAFSB-UHFFFAOYSA-N 0.000 claims description 2
- OTYNCFBIMOPRBT-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]butanamide Chemical compound C(CCC)(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC OTYNCFBIMOPRBT-UHFFFAOYSA-N 0.000 claims description 2
- QIOYUWITBFJOES-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]cyclobutanecarboxamide Chemical compound C1(CCC1)C(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC QIOYUWITBFJOES-UHFFFAOYSA-N 0.000 claims description 2
- QRYQHXRSKHELJJ-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]cyclohexanecarboxamide Chemical compound C1(CCCCC1)C(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC QRYQHXRSKHELJJ-UHFFFAOYSA-N 0.000 claims description 2
- DURORZYHZGDNML-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]cyclopentanecarboxamide Chemical compound C1(CCCC1)C(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC DURORZYHZGDNML-UHFFFAOYSA-N 0.000 claims description 2
- BIZPRFMEEMOSNC-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)OCC BIZPRFMEEMOSNC-UHFFFAOYSA-N 0.000 claims description 2
- VQPBJJRBTBYILE-UHFFFAOYSA-N N-[2-(2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]propanamide Chemical compound C(C)OC1=NC2=C(N1CCNC(CC)=O)C=C(C=C2)OC VQPBJJRBTBYILE-UHFFFAOYSA-N 0.000 claims description 2
- ASKLTMFCZWTEIQ-UHFFFAOYSA-N N-[2-(5-bromo-2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C(=C2)Br)OC)OCC ASKLTMFCZWTEIQ-UHFFFAOYSA-N 0.000 claims description 2
- BVSLRGAPRGQWNC-UHFFFAOYSA-N N-[2-(5-chloro-2,6-dimethoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C(=C2)Cl)OC)OC BVSLRGAPRGQWNC-UHFFFAOYSA-N 0.000 claims description 2
- LRRDNGSYVNSAEO-UHFFFAOYSA-N N-[2-(5-chloro-2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C(=C2)Cl)OC)OCC LRRDNGSYVNSAEO-UHFFFAOYSA-N 0.000 claims description 2
- ZJBOWGCBTCJJNG-UHFFFAOYSA-N N-[2-(5-chloro-2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NCCN1C(=NC2=C1C=C(C(=C2)Cl)OC)OCC ZJBOWGCBTCJJNG-UHFFFAOYSA-N 0.000 claims description 2
- SWMZGIRIHACCTN-UHFFFAOYSA-N N-[2-(6-methoxy-2-methylsulfanylbenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C=C(C=C2)OC)SC SWMZGIRIHACCTN-UHFFFAOYSA-N 0.000 claims description 2
- ZEHKUOUEYCAMRA-UHFFFAOYSA-N N-[2-(7-chloro-2-ethoxy-6-methoxybenzimidazol-1-yl)ethyl]acetamide Chemical compound C(C)(=O)NCCN1C(=NC2=C1C(=C(C=C2)OC)Cl)OCC ZEHKUOUEYCAMRA-UHFFFAOYSA-N 0.000 claims description 2
- IGBXTAHNBAVPGY-UHFFFAOYSA-N N-[3-(2,6-dimethoxybenzimidazol-1-yl)propyl]acetamide Chemical compound C(C)(=O)NCCCN1C(=NC2=C1C=C(C=C2)OC)OC IGBXTAHNBAVPGY-UHFFFAOYSA-N 0.000 claims description 2
- HJOUELOCKKMZBA-UHFFFAOYSA-N N-[3-(2-ethoxy-6-methoxybenzimidazol-1-yl)propyl]acetamide Chemical compound C(C)(=O)NCCCN1C(=NC2=C1C=C(C=C2)OC)OCC HJOUELOCKKMZBA-UHFFFAOYSA-N 0.000 claims description 2
- SGRBZRWEJGNQTA-UHFFFAOYSA-N N-[3-(5-chloro-2,6-dimethoxybenzimidazol-1-yl)propyl]acetamide Chemical compound C(C)(=O)NCCCN1C(=NC2=C1C=C(C(=C2)Cl)OC)OC SGRBZRWEJGNQTA-UHFFFAOYSA-N 0.000 claims description 2
- IYSSQVBXXUIIGE-UHFFFAOYSA-N N-[3-(5-chloro-2-ethoxy-6-methoxybenzimidazol-1-yl)propyl]acetamide Chemical compound C(C)(=O)NCCCN1C(=NC2=C1C=C(C(=C2)Cl)OC)OCC IYSSQVBXXUIIGE-UHFFFAOYSA-N 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 0 C*c([n](*N(*)C(*)=O)c1c2)nc1ccc2O* Chemical compound C*c([n](*N(*)C(*)=O)c1c2)nc1ccc2O* 0.000 description 45
- 229910052717 sulfur Chemical group 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 2
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 description 2
- 229960002629 agomelatine Drugs 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR102016024814A BR102016024814A2 (pt) | 2016-10-24 | 2016-10-24 | composto, processo de obtenção do composto, composição farmacêutica, uso do composto e método de tratamento de desordens psiquiátricas e/ou distúrbios do sono |
| BRBR1020160248140 | 2016-10-24 | ||
| PCT/BR2017/050320 WO2018076090A1 (en) | 2016-10-24 | 2017-10-23 | Compounds, process for obtaining the compounds, pharmaceutical composition, use of the compounds and method for treating psychiatric disorders and/or sleep disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019537624A JP2019537624A (ja) | 2019-12-26 |
| JP2019537624A5 true JP2019537624A5 (cg-RX-API-DMAC7.html) | 2020-11-26 |
| JP7194683B2 JP7194683B2 (ja) | 2022-12-22 |
Family
ID=62023150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019542758A Active JP7194683B2 (ja) | 2016-10-24 | 2017-10-23 | 化合物、化合物を得るための方法、医薬組成物、化合物の使用、ならびに精神医学的障害および／または睡眠障害を治療するための方法 |
Country Status (20)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR102016024814A2 (pt) * | 2016-10-24 | 2018-05-08 | Aché Laboratórios Farmacêuticos S.A. | composto, processo de obtenção do composto, composição farmacêutica, uso do composto e método de tratamento de desordens psiquiátricas e/ou distúrbios do sono |
| EP3433256B1 (en) | 2016-10-24 | 2019-08-07 | Astrazeneca AB | 6,7,8,9-tetrahydro-3h-pyrazolo[4,3-f]isoquinoline derivative useful in the treatment of cancer |
| CR20190379A (es) | 2017-01-30 | 2019-10-21 | Astrazeneca Ab | Moduladores del receptor de estrógeno |
| AR121842A1 (es) * | 2020-04-15 | 2022-07-13 | Ache Laboratorios Farmaceuticos Sa | Compuesto de benzimidazol para el tratamiento de trastornos metabólicos |
| CA3179907A1 (en) | 2020-04-24 | 2021-10-28 | Astrazeneca Ab | Dosage regimen for the treatment of cancer |
| BR112022021089A2 (pt) | 2020-04-24 | 2022-12-06 | Astrazeneca Ab | Formulações farmacêuticas |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5260051A (en) | 1990-12-17 | 1993-11-09 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising phosphate ester compounds containing a beneficial reagent component |
| FR2674524B1 (fr) | 1991-03-25 | 1993-05-21 | Adir | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2680366B1 (fr) | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9326192D0 (en) | 1993-12-22 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
| DE69528843T2 (de) * | 1994-06-10 | 2003-09-18 | Naucno-Issledovatel'skij Institut Farmakologii Akademii Medicinskich Nauk Sssr, Moskau/Moskva | Pharmakologisch aktive 2-mercaptobenzimidazolderivate |
| US5496826A (en) | 1994-09-02 | 1996-03-05 | Bristol-Myers Squibb Company | Pharmaceutical methods of using heterocyclic derivatives of N-phenylamides |
| FR2738818B1 (fr) | 1995-09-18 | 1997-12-05 | Valentonine | Nouveaux derives d'oxydation d'indolylalkylamines, et leur utilisation a titre de medicament |
| US6034239A (en) | 1996-03-08 | 2000-03-07 | Takeda Chemical Industries, Ltd. | Tricyclic compounds, their production and use |
| JP2884153B2 (ja) * | 1996-03-08 | 1999-04-19 | 武田薬品工業株式会社 | 三環性化合物、その製造法および剤 |
| AU719994B2 (en) | 1996-12-10 | 2000-05-18 | Bristol-Myers Squibb Company | Benzodioxole, benzofuran, dihydrobenzofuran, and benzodioxane melatonergic agents |
| WO1999062515A1 (en) | 1998-06-05 | 1999-12-09 | Bristol-Myers Squibb Company | Heterocyclic cis cyclopropane derivatives as melatonergic agents |
| CA2376949C (en) | 1999-06-30 | 2009-05-26 | Katherine S. Takaki | Heterocyclic aminopyrrolidine derivatives as melatonergic agents |
| WO2003062224A1 (en) * | 2002-01-17 | 2003-07-31 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
| EP1719761A4 (en) | 2004-02-23 | 2007-10-10 | Dainippon Sumitomo Pharma Co | NEW HETEROCYCLIC CONNECTION |
| ES2264641B1 (es) * | 2005-06-17 | 2008-03-01 | Quimica Sintetica, S.A. | Procedimiento para la obtencion de derivados de bencimidazol y sus intermedios. |
| US20090298811A1 (en) * | 2006-09-12 | 2009-12-03 | Pfizer Inc | Benzimidazolone derivatives |
| EP2088861A4 (en) * | 2006-10-25 | 2010-07-07 | Takeda Pharmaceutical | Benzimidazole compounds |
| RU2401831C2 (ru) * | 2008-12-15 | 2010-10-20 | Алла Хем, Ллс | Средство, снижающее влечение к алкоголю, фармацевтическая композиция и способы ее получения, лекарственное средство и способ лечения |
| BR102016024814A2 (pt) * | 2016-10-24 | 2018-05-08 | Aché Laboratórios Farmacêuticos S.A. | composto, processo de obtenção do composto, composição farmacêutica, uso do composto e método de tratamento de desordens psiquiátricas e/ou distúrbios do sono |
-
2016
- 2016-10-24 BR BR102016024814A patent/BR102016024814A2/pt not_active Application Discontinuation
-
2017
- 2017-07-19 UY UY0001040644A patent/UY40644A/es not_active Application Discontinuation
- 2017-07-19 UY UY0001037334A patent/UY37334A/es active IP Right Grant
- 2017-08-30 AR ARP170102402A patent/AR109467A1/es active IP Right Grant
- 2017-10-23 ES ES17865155T patent/ES2970546T3/es active Active
- 2017-10-23 CN CN201780079647.XA patent/CN110088092B/zh active Active
- 2017-10-23 AU AU2017351756A patent/AU2017351756B2/en active Active
- 2017-10-23 MX MX2019004782A patent/MX392990B/es unknown
- 2017-10-23 KR KR1020197011842A patent/KR102594251B1/ko active Active
- 2017-10-23 EP EP17865155.0A patent/EP3529234B1/en active Active
- 2017-10-23 SG SG11201903113TA patent/SG11201903113TA/en unknown
- 2017-10-23 ES ES20185268T patent/ES3013994T3/es active Active
- 2017-10-23 CN CN202210815568.3A patent/CN115181108A/zh active Pending
- 2017-10-23 JP JP2019542758A patent/JP7194683B2/ja active Active
- 2017-10-23 US US16/344,721 patent/US10781182B2/en active Active
- 2017-10-23 EP EP20185268.8A patent/EP3741760B1/en active Active
- 2017-10-23 PE PE2023002494A patent/PE20250558A1/es unknown
- 2017-10-23 FI FIEP17865155.0T patent/FI3529234T3/fi active
- 2017-10-23 DK DK17865155.0T patent/DK3529234T3/da active
- 2017-10-23 PT PT178651550T patent/PT3529234T/pt unknown
- 2017-10-23 PE PE2019000861A patent/PE20191046A1/es unknown
- 2017-10-23 WO PCT/BR2017/050320 patent/WO2018076090A1/en not_active Ceased
- 2017-10-23 SG SG10202009001TA patent/SG10202009001TA/en unknown
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2019
- 2019-04-23 CL CL2019001105A patent/CL2019001105A1/es unknown
- 2019-05-09 CO CONC2019/0004756A patent/CO2019004756A2/es unknown
- 2019-05-09 EC ECSENADI201932963A patent/ECSP19032963A/es unknown
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2020
- 2020-05-13 US US15/930,990 patent/US11091445B2/en active Active