HRP20220234T1 - Kristalni oblici - Google Patents
Kristalni oblici Download PDFInfo
- Publication number
- HRP20220234T1 HRP20220234T1 HRP20220234TT HRP20220234T HRP20220234T1 HR P20220234 T1 HRP20220234 T1 HR P20220234T1 HR P20220234T T HRP20220234T T HR P20220234TT HR P20220234 T HRP20220234 T HR P20220234T HR P20220234 T1 HRP20220234 T1 HR P20220234T1
- Authority
- HR
- Croatia
- Prior art keywords
- 4carbonyl
- phosphono
- pyrrolidin
- propionyl
- piperazine
- Prior art date
Links
- PKIFIIJFQKTNCT-IUQUCOCYSA-N [(2R)-3-(4-butoxycarbonylpiperazin-1-yl)-2-[[6-[(3S)-3-methoxypyrrolidin-1-yl]-2-phenylpyrimidine-4-carbonyl]amino]-3-oxopropyl]phosphonic acid hydrochloride Chemical compound Cl.CCCCOC(=O)N1CCN(CC1)C(=O)[C@H](CP(O)(O)=O)NC(=O)c1cc(nc(n1)-c1ccccc1)N1CC[C@@H](C1)OC PKIFIIJFQKTNCT-IUQUCOCYSA-N 0.000 claims 11
- 239000013078 crystal Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 4
- 239000012454 non-polar solvent Substances 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 3
- 201000004569 Blindness Diseases 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 208000032382 Ischaemic stroke Diseases 0.000 claims 3
- 206010034576 Peripheral ischaemia Diseases 0.000 claims 3
- 208000032109 Transient ischaemic attack Diseases 0.000 claims 3
- 206010001902 amaurosis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 201000010875 transient cerebral ischemia Diseases 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 238000010586 diagram Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- FYXHWMQPCJOJCH-GMAHTHKFSA-N selatogrel Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CP(O)(O)=O)NC(=O)C1=CC(N2C[C@H](CC2)OC)=NC(C=2C=CC=CC=2)=N1 FYXHWMQPCJOJCH-GMAHTHKFSA-N 0.000 claims 2
- 150000001348 alkyl chlorides Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000002178 crystalline material Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida, naznačen prisustvom maksimuma u dijagramu rendgenske difrakcije na prahu pri sljedećim kutovima refrakcije 2θ: 4,0°, 5,0°, i 15,3°.
2. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema patentnom zahtjevu 1, naznačen prisustvom maksimuma u dijagramu rendgenske difrakcije na prahu pri sljedećim kutovima refrakcije 2θ: 4,0°, 5,0°, 11,7°, 15,3°, i 19,3°.
3. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema patentnom zahtjevu 1, naznačen prisustvom maksimuma u dijagramu rendgenske difrakcije na prahu pri sljedećim kutovima refrakcije 2θ: 4,0°, 5,0°, 5,9°, 11,7°, 15,3°, 16,9°, 19,3°, 19,7°, i 20,7°.
4. Postupak za proizvodnju 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida u kristalnom obliku prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da postupak obuhvaća sljedeće korake:
a. dodavanje acetona (10 do 30 vol.) u otopinu koja sadrži 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorid i nepolarno otapalo (0,5 do 3,0 vol.) pri 45 do 60°C, pri čemu se nepolarno otapalo bira od (C1-2)kloroalkana;
b. dodavanje vode (0,3 do 0,7 vol.) pri 45 do 60°C;
c. miješanje smjese uz hlađenje sa temperature od 45 do 60°C do temperature na ili ispod 30°C u periodu od najmanje jednog sata; i
d. izoliranje dobivenog kristalnog materijala.
5. Postupak prema patentnom zahtjevu 4, naznačen time, da količina nepolarnog otapala u koraku a. iznosi 1,0 do 2,0 vol. i pritom nepolarno otapalo jest diklorometan.
6. Postupak prema bilo kojem od patentnih zahtjeva 4 ili 5, naznačen time, da se smjesa miješa u koraku c. u periodu između jednoga i četiri sata na temperaturi od 45 do 60°C i naknadno se hladi do temperature koja je između 20 i 30°C u vremenskom periodu od jednoga do dva sata.
7. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je za uporabu kao lijek.
8. Farmaceutski pripravak, naznačen time, da kao aktivni sastojak sadrži kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3, i najmanje jedan farmaceutski prihvatljiv nosač.
9. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je za uporabu u proizvodnji farmaceutskog pripravka, pri čemu navedeni farmaceutski pripravak kao aktivni sastojak sadrži 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorid, i najmanje jedan farmaceutski prihvatljivi nosivi materijal.
10. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je za uporabu u prevenciji ili liječenju bolesti odabrane iz skupine koju čine akutni koronarni sindromi, periferna ishemija, amauroza, ishemijski moždani udar i prolazni ishemijski napad.
11. 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester, ili njegova farmaceutski prihvatljiva sol, naznačen time, da je za uporabu u prevenciji ili liječenju bolesti odabrane iz skupine koju čine akutni koronarni sindromi, periferna ishemija, amauroza, ishemijski moždani udar i prolazni ishemijski napad, pri čemu se 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester, ili njegova farmaceutski prihvatljiva sol, dobiva iz kristalnog oblika 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3.
12. Kristalni oblik 4-((R)-2-{[6-((S)-3-metoksi-pirolidin-1-il)-2-fenil-pirimidin-4karbonil]-amino}-3-fosfono-propionil)-piperazin-1-karboksilna kiselina butil ester hidroklorida prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je za uporabu u proizvodnji farmaceutskog pripravka za prevenciju ili liječenje bolesti odabrane iz skupine koju čine akutni koronarni sindromi, periferna ishemija, amauroza, ishemijski moždani udar i prolazni ishemijski napad.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2016072562 | 2016-09-22 | ||
| PCT/EP2017/073858 WO2018055016A1 (en) | 2016-09-22 | 2017-09-21 | Crystalline forms |
| EP17771436.7A EP3515924B1 (en) | 2016-09-22 | 2017-09-21 | Crystalline forms |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220234T1 true HRP20220234T1 (hr) | 2022-05-13 |
Family
ID=59923448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220234TT HRP20220234T1 (hr) | 2016-09-22 | 2017-09-21 | Kristalni oblici |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US10730896B2 (hr) |
| EP (2) | EP3981774A1 (hr) |
| JP (1) | JP7097369B2 (hr) |
| KR (1) | KR102552795B1 (hr) |
| CN (1) | CN109715639B (hr) |
| AU (1) | AU2017331930B2 (hr) |
| BR (1) | BR112019004845A2 (hr) |
| CA (1) | CA3037794A1 (hr) |
| CL (1) | CL2019000728A1 (hr) |
| DK (1) | DK3515924T3 (hr) |
| EA (1) | EA201990723A1 (hr) |
| ES (1) | ES2908572T3 (hr) |
| HR (1) | HRP20220234T1 (hr) |
| HU (1) | HUE057772T2 (hr) |
| IL (1) | IL265445B2 (hr) |
| LT (1) | LT3515924T (hr) |
| MA (1) | MA46266B1 (hr) |
| MX (1) | MX2019003093A (hr) |
| MY (1) | MY193080A (hr) |
| PH (1) | PH12019500567A1 (hr) |
| PL (1) | PL3515924T3 (hr) |
| PT (1) | PT3515924T (hr) |
| RS (1) | RS62946B1 (hr) |
| SI (1) | SI3515924T1 (hr) |
| TW (1) | TWI752086B (hr) |
| UA (1) | UA124073C2 (hr) |
| WO (1) | WO2018055016A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3050831A1 (en) | 2017-03-15 | 2018-09-20 | Idorsia Pharmaceuticals Ltd | Subcutaneous administration of a p2y12 receptor antagonist |
| TW202216150A (zh) | 2020-07-15 | 2022-05-01 | 瑞士商愛杜西亞製藥有限公司 | 包含p2y12受體拮抗劑的水性醫藥組合物 |
| KR20240033005A (ko) | 2021-07-13 | 2024-03-12 | 이도르시아 파마슈티컬스 리미티드 | 4-((r)-2-｛[6-((s)-3-메톡시-피롤리딘-1-일)-2-페닐-피리미딘-4-카르보닐]-아미노｝-3-포스포노-프로피오닐)-피페라진-1-카르복실산부틸 에스테르의 합성 방법 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5373586A (en) | 1976-12-09 | 1978-06-30 | Mitsubishi Chem Ind Ltd | New penicillin derivatives |
| CA2020437A1 (en) | 1989-07-05 | 1991-01-06 | Yoshihide Fuse | Cinnamamide derivative |
| AU5414000A (en) | 1999-06-14 | 2001-01-02 | Eli Lilly And Company | Compounds |
| US6861424B2 (en) | 2001-06-06 | 2005-03-01 | Schering Aktiengesellschaft | Platelet adenosine diphosphate receptor antagonists |
| EA200500899A1 (ru) | 2002-12-11 | 2006-02-24 | Шеринг Акциенгезельшафт | Антагонисты аденозиндифосфатного рецептора тромбоцитов |
| DE602004029146D1 (de) | 2003-04-09 | 2010-10-28 | Wyeth Llc | Derivate von 2-(8,9-dioxo-2,6-diazabicyclo(5.2.0)non-1(7)-en-2-yl)alkylphosphonsäure und deren verwendung als n-methyl-d-aspartat- (nmda-) rezeptorantagonisten |
| TW200640877A (en) | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| CN101300241A (zh) | 2005-10-21 | 2008-11-05 | 埃科特莱茵药品有限公司 | 作为抗疟疾剂的哌嗪衍生物 |
| CL2007002920A1 (es) | 2006-10-13 | 2008-06-06 | Actelion Pharmaceuticals Ltd | Compuestos derivados de 2-aminocarbonilpiridina; composicion farmaceutica; y uso para el tratamiento de trastornos vasculares oclusivos. |
| AR063518A1 (es) | 2006-10-25 | 2009-01-28 | Actelion Pharmaceuticals Ltd | Derivados 2-fenil-6-aminocarbonil-pirimidina; composicion farmaceutica; y su uso para tratar y/o prevenir enfermedades vasculares perifericas viscerales, hepaticas y renales, enfermedades cardiovasculares y enfermedades cerebrovasculares asociados con la agregacion de plaquetas, incluyendo trombosis |
| JP4785881B2 (ja) | 2007-02-27 | 2011-10-05 | 大塚製薬株式会社 | 医薬 |
| CN101663293B (zh) | 2007-04-23 | 2013-07-31 | 塞诺菲-安万特股份有限公司 | 作为p2y12拮抗剂的喹啉-甲酰胺衍生物 |
| PT2225253E (pt) | 2007-11-29 | 2012-09-19 | Actelion Pharmaceuticals Ltd | Derivados de ácido fosfónico e respetiva utilização como antagonistas do recetor p2y12 |
| JP5504171B2 (ja) | 2007-12-26 | 2014-05-28 | サノフイ | Ｐ２ｙ１２アンタゴニストとしてのヘテロサイクリックピラゾール−カルボキサミド |
| EP2238127B1 (en) | 2007-12-26 | 2012-08-15 | Sanofi | Pyrazole-carboxamide derivatives as p2y12 antagonists |
| AR071652A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2- fenil-piridina substituidos |
| AR071653A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2-fenil-4-ciclopropil-pirimidina |
| US8288385B2 (en) | 2009-04-08 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | 6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidines |
| US8664203B2 (en) | 2009-04-22 | 2014-03-04 | Actelion Pharmaceuticals Ltd. | Thiazole derivatives and their use as P2Y12 receptor antagonists |
| CA3050831A1 (en) | 2017-03-15 | 2018-09-20 | Idorsia Pharmaceuticals Ltd | Subcutaneous administration of a p2y12 receptor antagonist |
-
2017
- 2017-09-21 MA MA46266A patent/MA46266B1/fr unknown
- 2017-09-21 WO PCT/EP2017/073858 patent/WO2018055016A1/en unknown
- 2017-09-21 US US16/335,973 patent/US10730896B2/en active Active
- 2017-09-21 HU HUE17771436A patent/HUE057772T2/hu unknown
- 2017-09-21 MY MYPI2019001474A patent/MY193080A/en unknown
- 2017-09-21 AU AU2017331930A patent/AU2017331930B2/en active Active
- 2017-09-21 IL IL265445A patent/IL265445B2/en unknown
- 2017-09-21 ES ES17771436T patent/ES2908572T3/es active Active
- 2017-09-21 RS RS20220163A patent/RS62946B1/sr unknown
- 2017-09-21 HR HRP20220234TT patent/HRP20220234T1/hr unknown
- 2017-09-21 TW TW106132387A patent/TWI752086B/zh active
- 2017-09-21 KR KR1020197011330A patent/KR102552795B1/ko active IP Right Grant
- 2017-09-21 EA EA201990723A patent/EA201990723A1/ru unknown
- 2017-09-21 EP EP21206477.8A patent/EP3981774A1/en not_active Withdrawn
- 2017-09-21 CA CA3037794A patent/CA3037794A1/en active Pending
- 2017-09-21 SI SI201731102T patent/SI3515924T1/sl unknown
- 2017-09-21 PL PL17771436T patent/PL3515924T3/pl unknown
- 2017-09-21 JP JP2019536696A patent/JP7097369B2/ja active Active
- 2017-09-21 DK DK17771436.7T patent/DK3515924T3/da active
- 2017-09-21 LT LTEPPCT/EP2017/073858T patent/LT3515924T/lt unknown
- 2017-09-21 UA UAA201903751A patent/UA124073C2/uk unknown
- 2017-09-21 MX MX2019003093A patent/MX2019003093A/es unknown
- 2017-09-21 BR BR112019004845A patent/BR112019004845A2/pt unknown
- 2017-09-21 EP EP17771436.7A patent/EP3515924B1/en active Active
- 2017-09-21 CN CN201780057793.2A patent/CN109715639B/zh active Active
- 2017-09-21 PT PT177714367T patent/PT3515924T/pt unknown
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2019
- 2019-03-15 PH PH12019500567A patent/PH12019500567A1/en unknown
- 2019-03-21 CL CL2019000728A patent/CL2019000728A1/es unknown
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2020
- 2020-07-24 US US16/938,730 patent/US11365209B2/en active Active
-
2022
- 2022-05-10 US US17/741,427 patent/US20220275011A1/en active Pending
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