MA38801B1 - Nouveaux composés isoindoline ou isoquinoléine, procédé pour leur préparation et compositions pharmaceutiques les contenant - Google Patents
Nouveaux composés isoindoline ou isoquinoléine, procédé pour leur préparation et compositions pharmaceutiques les contenantInfo
- Publication number
- MA38801B1 MA38801B1 MA38801A MA38801A MA38801B1 MA 38801 B1 MA38801 B1 MA 38801B1 MA 38801 A MA38801 A MA 38801A MA 38801 A MA38801 A MA 38801A MA 38801 B1 MA38801 B1 MA 38801B1
- Authority
- MA
- Morocco
- Prior art keywords
- preparation
- pharmaceutical compositions
- compositions containing
- isoquinoline compounds
- novel isoindoline
- Prior art date
Links
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 210000000987 immune system Anatomy 0.000 abstract 1
- 230000000861 pro-apoptotic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
- A61N5/00—Radiation therapy
- A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Pathology (AREA)
- Radiology & Medical Imaging (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Abstract
L'invention concerne des composés de formule (i) : (i) dans laquelle het, r3, r4, r5, r7, r8, r9, t, p, p', q, et q' sont tels que définis dans la description, des agents pro-apoptotiques utiles dans le traitement de cancers et de maladies auto-immunes et des maladies du système immunitaire.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1357276A FR3008977A1 (fr) | 2013-07-23 | 2013-07-23 | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
PCT/EP2014/065764 WO2015011164A1 (fr) | 2013-07-23 | 2014-07-22 | Nouveaux composés isoindoline ou isoquinoléine, procédé pour leur préparation et compositions pharmaceutiques les contenant |
Publications (2)
Publication Number | Publication Date |
---|---|
MA38801A1 MA38801A1 (fr) | 2018-05-31 |
MA38801B1 true MA38801B1 (fr) | 2019-03-29 |
Family
ID=49911606
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MA38801A MA38801B1 (fr) | 2013-07-23 | 2014-07-22 | Nouveaux composés isoindoline ou isoquinoléine, procédé pour leur préparation et compositions pharmaceutiques les contenant |
Country Status (49)
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3008977A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
MX2018012840A (es) | 2016-04-20 | 2019-03-11 | Squibb Bristol Myers Co | Compuestos heterociclicos biciclicos sustituidos. |
PE20211804A1 (es) | 2018-06-27 | 2021-09-14 | Proteostasis Therapeutics Inc | Compuestos que aumentan la actividad del proteosoma |
CN112010796B (zh) * | 2020-09-17 | 2022-04-22 | 浙江大学 | 光学活性3-(1,1-二氟-2-氧-2-芳基乙基)异吲哚啉-1-酮衍生物制备方法 |
WO2023161317A1 (fr) | 2022-02-24 | 2023-08-31 | Les Laboratoires Servier | Dérivés de 5-[7-(3,4-dihydro-1h-isoquinoline-2-carbonyl)-1,2,3,4 tétrahydroisoquinolin-6-y l]-1h-pyrrole-3-carboxamide, compositions pharmaceutiques les contenant et leurs utilisations en tant qu'agents pro-apoptotiques |
WO2023225359A1 (fr) | 2022-05-20 | 2023-11-23 | Novartis Ag | Conjugués anticorps-médicament de composés anti-cancéreux et procédés d'utilisation |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4901102B2 (ja) | 2002-05-03 | 2012-03-21 | エクセリクシス, インク. | プロテインキナーゼモジュレーターおよびその使用方法 |
WO2004096774A1 (fr) * | 2003-05-01 | 2004-11-11 | Glaxo Group Limited | Derives d'acyle isoindoline et d'acyle isoquinoline utilises comme agents antiviraux |
US20050070570A1 (en) | 2003-06-18 | 2005-03-31 | 4Sc Ag | Novel potassium channels modulators |
MX2007002104A (es) * | 2004-08-20 | 2007-10-10 | Univ Michigan | Inhibidores de moleculas pequenas de los miembros de la familia bcl-2 anti-apoptoticos, y usos de los mismos. |
WO2006023778A2 (fr) * | 2004-08-20 | 2006-03-02 | The Regents Of The University Of Michigan | Petits inhibiteurs moleculaires de membres de la famille des anti-apoptose bcl-2, et utilisations correspondantes |
KR20070107000A (ko) * | 2005-02-15 | 2007-11-06 | 노보 노르디스크 에이/에스 | 3,4-디히드로-1h-이소퀴놀린-2-카르복실산5-아미노피리딘-2-일 에스테르 |
US8445679B2 (en) | 2007-04-16 | 2013-05-21 | Abbvie Inc. | 7-substituted indole MCL-1 inhibitors |
AU2008334075A1 (en) | 2007-11-30 | 2009-06-11 | Biota Scientific Management Pty Ltd | Tetrahydro-isoquinoline PPAT inhibitors as antibacterial agents |
US20090221612A1 (en) | 2008-02-13 | 2009-09-03 | Mitchell Scott A | Certain substituted amides, method of making, and method of use thereof |
US7984530B2 (en) | 2008-02-14 | 2011-07-26 | Tory Reynolds | Pet waste vacuum system and apparatus, disposable liners therefor, and a method of collecting pet waste using same |
CN103732589B (zh) * | 2011-05-25 | 2016-03-30 | 百时美施贵宝公司 | 可用作抗细胞凋亡bcl抑制剂的取代的磺酰胺 |
EA201491264A1 (ru) * | 2011-12-23 | 2014-11-28 | Новартис Аг | Соединения для ингибирования взаимодействия bcl-2 с партнерами по связыванию |
US10228738B2 (en) | 2011-12-27 | 2019-03-12 | Intel Corporation | Methods and systems to control power gates during an active state of a gated domain based on load conditions of the gated domain |
FR2986002B1 (fr) * | 2012-01-24 | 2014-02-21 | Servier Lab | Nouveaux derives d'indolizine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR3008979B1 (fr) * | 2013-07-23 | 2015-07-24 | Servier Lab | Nouveaux derives phosphates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR3008977A1 (fr) * | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives d'isoindoline ou d'isoquinoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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2013
- 2013-07-23 FR FR1357276A patent/FR3008977A1/fr not_active Withdrawn
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2014
- 2014-07-13 JO JOP/2014/0223A patent/JO3457B1/ar active
- 2014-07-15 UY UY0001035664A patent/UY35664A/es active IP Right Grant
- 2014-07-22 SI SI201431038T patent/SI3024826T1/sl unknown
- 2014-07-22 TN TN2016000003A patent/TN2016000003A1/en unknown
- 2014-07-22 US US14/905,985 patent/US9809574B2/en active Active
- 2014-07-22 PL PL14741648T patent/PL3024826T3/pl unknown
- 2014-07-22 MY MYPI2016700106A patent/MY193619A/en unknown
- 2014-07-22 BR BR112016001080-9A patent/BR112016001080B1/pt active IP Right Grant
- 2014-07-22 NZ NZ716155A patent/NZ716155A/en unknown
- 2014-07-22 HU HUE14741648A patent/HUE041443T2/hu unknown
- 2014-07-22 PT PT14741648T patent/PT3024826T/pt unknown
- 2014-07-22 TR TR2018/19155T patent/TR201819155T4/tr unknown
- 2014-07-22 AP AP2016008989A patent/AP2016008989A0/xx unknown
- 2014-07-22 CN CN201480042422.3A patent/CN105431422B/zh active Active
- 2014-07-22 CN CN201811358313.9A patent/CN109456324B/zh active Active
- 2014-07-22 CU CUP2016000010A patent/CU24352B1/xx unknown
- 2014-07-22 EP EP14741648.1A patent/EP3024826B1/fr active Active
- 2014-07-22 GE GEAP201414063A patent/GEP20207070B/en unknown
- 2014-07-22 UA UAA201601395A patent/UA117490C2/uk unknown
- 2014-07-22 TW TW103125161A patent/TWI560184B/zh active
- 2014-07-22 KR KR1020167004570A patent/KR102008431B1/ko active IP Right Grant
- 2014-07-22 SG SG11201600205XA patent/SG11201600205XA/en unknown
- 2014-07-22 LT LTEP14741648.1T patent/LT3024826T/lt unknown
- 2014-07-22 EA EA201600122A patent/EA032301B1/ru unknown
- 2014-07-22 CA CA2919572A patent/CA2919572C/fr active Active
- 2014-07-22 AU AU2014295101A patent/AU2014295101B2/en active Active
- 2014-07-22 MD MDA20160018A patent/MD4793C1/ro active IP Right Grant
- 2014-07-22 PE PE2016000023A patent/PE20160241A1/es unknown
- 2014-07-22 ES ES14741648T patent/ES2711371T3/es active Active
- 2014-07-22 ME MEP-2019-35A patent/ME03346B/fr unknown
- 2014-07-22 MX MX2016000904A patent/MX365373B/es active IP Right Grant
- 2014-07-22 AR ARP140102713A patent/AR097009A1/es active IP Right Grant
- 2014-07-22 RU RU2016106003A patent/RU2689305C2/ru active
- 2014-07-22 DK DK14741648.1T patent/DK3024826T3/en active
- 2014-07-22 RS RS20190150A patent/RS58344B1/sr unknown
- 2014-07-22 WO PCT/EP2014/065764 patent/WO2015011164A1/fr active Application Filing
- 2014-07-22 MA MA38801A patent/MA38801B1/fr unknown
- 2014-07-22 JP JP2016528512A patent/JP6395829B2/ja active Active
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2016
- 2016-01-03 IL IL243449A patent/IL243449A0/en active IP Right Grant
- 2016-01-06 PH PH12016500034A patent/PH12016500034A1/en unknown
- 2016-01-11 DO DO2016000009A patent/DOP2016000009A/es unknown
- 2016-01-11 ZA ZA2016/00198A patent/ZA201600198B/en unknown
- 2016-01-15 CR CR20160030A patent/CR20160030A/es unknown
- 2016-01-20 CL CL2016000148A patent/CL2016000148A1/es unknown
- 2016-01-21 NI NI201600016A patent/NI201600016A/es unknown
- 2016-01-21 SA SA516370439A patent/SA516370439B1/ar unknown
- 2016-06-13 HK HK16106761.6A patent/HK1218754A1/zh unknown
- 2016-09-21 HK HK16111083.7A patent/HK1222856A1/zh unknown
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2017
- 2017-09-14 US US15/704,330 patent/US10689364B2/en active Active
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2019
- 2019-02-11 CY CY20191100175T patent/CY1121247T1/el unknown
- 2019-02-12 HR HRP20190277TT patent/HRP20190277T1/hr unknown
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2020
- 2020-05-04 US US16/865,799 patent/US11028070B2/en active Active
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