PE20211917A1 - Biarilamidas con grupos de azucar modificados para el tratamiento de enfermedades asociadas con la trayectoria de la proteina de choque de calor - Google Patents
Biarilamidas con grupos de azucar modificados para el tratamiento de enfermedades asociadas con la trayectoria de la proteina de choque de calorInfo
- Publication number
- PE20211917A1 PE20211917A1 PE2020001859A PE2020001859A PE20211917A1 PE 20211917 A1 PE20211917 A1 PE 20211917A1 PE 2020001859 A PE2020001859 A PE 2020001859A PE 2020001859 A PE2020001859 A PE 2020001859A PE 20211917 A1 PE20211917 A1 PE 20211917A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- carboxy
- halo
- treatment
- alkenyl
- Prior art date
Links
- 102000002812 Heat-Shock Proteins Human genes 0.000 title 1
- 108010004889 Heat-Shock Proteins Proteins 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 abstract 1
- 208000012902 Nervous system disease Diseases 0.000 abstract 1
- 208000025966 Neurological disease Diseases 0.000 abstract 1
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 1
- -1 biaryl amides Chemical class 0.000 abstract 1
- 125000005841 biaryl group Chemical group 0.000 abstract 1
- 235000001671 coumarin Nutrition 0.000 abstract 1
- 150000004775 coumarins Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 210000005036 nerve Anatomy 0.000 abstract 1
- 230000004770 neurodegeneration Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/11—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Esta referido a compuestos a base de biaril amidas y cumarinas con grupos de azucar modificados de Formula I, II, III, IV o V, en donde: n es 0, 1, 2; X1 es CR14 o N; X2 es CR15 o N; Y1 es alcandiilo, CO-alcandiilo; Y2 es CH2, O, o S; R1, R2 son H, amino, halo, OH, carboxi, entre otros; R3 es -NR11R11', -C(O)NR12R12'; R4, R5, R6 son H, halo, alquilo, alcoxi, aciloxi; R7 es carboxi, alquilo, alquenilo, entre otros; R7' es H, carboxi, alquilo, alquenilo, entre otros; R8, R9, R10 son H, halo, OH, alquilo, alcoxi, entre otros; R16 es alquilo, cicloalquilo, arilo, heteroarilo; R17, R18 son H, alquilo; R19 es carboxi, alquilo, alquenilo, entre otros; R19' es H, carboxi, alquilo, alquenilo, entre otros; R20, R21, R22 son halo, OH, alquilo, alcoxi, entre otros. Estos compuestos son inhibidores de biaril Hsp 90 con grupos de eter modificados y son utiles para el tratamiento y prevencion de enfermedades y trastornos, que incluyen trastornos neurologicos, tales como enfermedades neurodegenerativas y trastornos que danan el nervio, por ejemplo, neuropatia periferica diabetica.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862671047P | 2018-05-14 | 2018-05-14 | |
| PCT/US2019/032292 WO2019222269A1 (en) | 2018-05-14 | 2019-05-14 | Biaryl amides with modified sugar groups for treatment of diseases associated with heat shock protein pathway |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20211917A1 true PE20211917A1 (es) | 2021-09-28 |
Family
ID=67002352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2020001859A PE20211917A1 (es) | 2018-05-14 | 2019-05-14 | Biarilamidas con grupos de azucar modificados para el tratamiento de enfermedades asociadas con la trayectoria de la proteina de choque de calor |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US11827664B2 (es) |
| EP (1) | EP3794009A1 (es) |
| KR (1) | KR20210021457A (es) |
| CN (1) | CN112513058A (es) |
| AU (1) | AU2019271126A1 (es) |
| BR (1) | BR112020023277A2 (es) |
| CA (1) | CA3100333A1 (es) |
| CL (1) | CL2020002957A1 (es) |
| CO (1) | CO2020015380A2 (es) |
| EA (1) | EA202092727A1 (es) |
| IL (2) | IL309891A (es) |
| MX (1) | MX2020012366A (es) |
| PE (1) | PE20211917A1 (es) |
| PH (1) | PH12020551941A1 (es) |
| SG (1) | SG11202011311YA (es) |
| WO (1) | WO2019222269A1 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA125163C2 (uk) | 2018-05-14 | 2022-01-19 | Гіліад Сайєнсіз, Інк. | Інгібітори mcl-1 |
| TWI778443B (zh) | 2019-11-12 | 2022-09-21 | 美商基利科學股份有限公司 | Mcl1抑制劑 |
| EP4065567A1 (en) | 2019-11-26 | 2022-10-05 | Gilead Sciences, Inc. | Processes and intermediates for preparing mcl1 inhibitors |
| US20230138729A1 (en) * | 2021-09-13 | 2023-05-04 | Rubedo Life Sciences, Inc. | Coumarin Derivatives of Sugar Analogs and Uses Thereof |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06501465A (ja) | 1990-09-07 | 1994-02-17 | シェリング・コーポレーション | 抗ウイルス化合物 |
| FR2792320B1 (fr) | 1999-04-19 | 2003-05-09 | Hoechst Marion Roussel Inc | Nouveaux amides aromatiques substitues par un ribose, leur procede de preparation et leur application comme medicaments |
| US7053060B2 (en) | 2000-11-30 | 2006-05-30 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| US7208630B2 (en) | 2004-10-27 | 2007-04-24 | University Of Kansas | Heat shock protein 90 inhibitors |
| US7608594B2 (en) | 2004-11-03 | 2009-10-27 | University Of Kansas | Novobiocin analogues as anticancer agents |
| WO2010096650A1 (en) | 2009-02-20 | 2010-08-26 | University Of Kansas | Novobiocin analogues having modified sugar moieties |
| US7622451B2 (en) | 2004-11-03 | 2009-11-24 | University Of Kansas | Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders |
| US9120774B2 (en) | 2004-11-03 | 2015-09-01 | University Of Kansas | Novobiocin analogues having modified sugar moieties |
| US8212012B2 (en) | 2004-11-03 | 2012-07-03 | University Of Kansas | Novobiocin analogues having modified sugar moieties |
| US8212011B2 (en) | 2004-11-03 | 2012-07-03 | University Of Kansas | Novobiocin analogues |
| DE602006017566D1 (de) | 2005-08-30 | 2010-11-25 | Boehringer Ingelheim Pharma | Glucopyranosyl-substituierte benzyl-derivate, medikamente mit solchen verbindungen, ihre verwendung und herstellungsverfahren dafür |
| US8044041B2 (en) | 2006-11-15 | 2011-10-25 | Forest Laboratories Holdings Limited | Phthalazine derivatives as inhibitors of protein kinase |
| DE102007002715A1 (de) * | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Triazolderivat |
| RS52978B (en) | 2007-03-20 | 2014-02-28 | Curis, Inc. | FUSIONED AMINO PIRIDIN AS HSP90 INHIBITORS |
| US7960353B2 (en) | 2007-05-10 | 2011-06-14 | University Of Kansas | Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders |
| WO2010014617A1 (en) | 2008-07-28 | 2010-02-04 | University Of Kansas | Heat shock protein 90 inhibitor dosing methods |
| WO2011041593A1 (en) | 2009-09-30 | 2011-04-07 | University Of Kansas | Novobiocin analogues and treatment of polycystic kidney disease |
| EP2594554A4 (en) | 2010-07-13 | 2014-01-15 | Dainippon Sumitomo Pharma Co | BIARYLAMID DERIVATIVES BZW. PHARMACEUTICALLY PERMITTED SALT FROM THIS |
| CA2832099C (en) | 2011-04-05 | 2019-07-09 | Sloan-Kettering Institute For Cancer Research | Hsp90 inhibitors |
| US9056104B2 (en) | 2011-05-20 | 2015-06-16 | The University Of Kansas | Dynamic inhibitors of heat shock protein 90 |
| PL2812341T3 (pl) | 2012-02-09 | 2020-03-31 | The University Of Kansas | Inhibitory C-końcowe HSP90 |
| WO2014181359A1 (en) | 2013-05-09 | 2014-11-13 | Council Of Scientific & Industrial Research | A process for the preparation of an anticonvulsant agent pregabalin hydrochloride |
| US10689344B2 (en) | 2013-11-07 | 2020-06-23 | University Of Kansas | Biphenylamide derivative Hsp90 inhibitors |
| EP3068778A2 (en) | 2013-11-11 | 2016-09-21 | The University of Kansas | Coumarin based hsp90 inhibitors with urea and ether substituents |
| US9994556B2 (en) | 2014-06-13 | 2018-06-12 | University Of Kansas | Triazole modified coumarin and biphenyl amide-based HSP90 inhibitors |
| US10590065B2 (en) * | 2014-06-24 | 2020-03-17 | University Of Kansas | Biphenyl amides with modified ether groups as HSP90 inhibitors and HSP70 inducers |
-
2019
- 2019-05-14 IL IL309891A patent/IL309891A/en unknown
- 2019-05-14 KR KR1020207033977A patent/KR20210021457A/ko active Search and Examination
- 2019-05-14 BR BR112020023277-7A patent/BR112020023277A2/pt unknown
- 2019-05-14 WO PCT/US2019/032292 patent/WO2019222269A1/en unknown
- 2019-05-14 AU AU2019271126A patent/AU2019271126A1/en active Pending
- 2019-05-14 CA CA3100333A patent/CA3100333A1/en active Pending
- 2019-05-14 EP EP19732770.3A patent/EP3794009A1/en active Pending
- 2019-05-14 IL IL278698A patent/IL278698B2/en unknown
- 2019-05-14 PE PE2020001859A patent/PE20211917A1/es unknown
- 2019-05-14 CN CN201980046311.2A patent/CN112513058A/zh active Pending
- 2019-05-14 EA EA202092727A patent/EA202092727A1/ru unknown
- 2019-05-14 US US17/055,331 patent/US11827664B2/en active Active
- 2019-05-14 MX MX2020012366A patent/MX2020012366A/es unknown
- 2019-05-14 SG SG11202011311YA patent/SG11202011311YA/en unknown
-
2020
- 2020-11-13 CL CL2020002957A patent/CL2020002957A1/es unknown
- 2020-11-13 PH PH12020551941A patent/PH12020551941A1/en unknown
- 2020-12-09 CO CONC2020/0015380A patent/CO2020015380A2/es unknown
-
2023
- 2023-10-12 US US18/485,699 patent/US20240182507A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PH12020551941A1 (en) | 2021-08-16 |
| BR112020023277A2 (pt) | 2021-02-23 |
| KR20210021457A (ko) | 2021-02-26 |
| IL278698B2 (en) | 2024-06-01 |
| MX2020012366A (es) | 2021-02-09 |
| US11827664B2 (en) | 2023-11-28 |
| CN112513058A (zh) | 2021-03-16 |
| CA3100333A1 (en) | 2019-11-21 |
| IL278698B1 (en) | 2024-02-01 |
| EA202092727A1 (ru) | 2021-04-20 |
| AU2019271126A1 (en) | 2020-12-10 |
| IL309891A (en) | 2024-03-01 |
| CL2020002957A1 (es) | 2021-04-16 |
| US20240182507A1 (en) | 2024-06-06 |
| JP2021524439A (ja) | 2021-09-13 |
| US20210261592A1 (en) | 2021-08-26 |
| EP3794009A1 (en) | 2021-03-24 |
| CO2020015380A2 (es) | 2020-12-21 |
| WO2019222269A1 (en) | 2019-11-21 |
| IL278698A (es) | 2021-01-31 |
| SG11202011311YA (en) | 2020-12-30 |
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