RU2616619C2 - Морфолино-замещенные производные мочевины или карбамата в качестве ингибиторов mtor - Google Patents
Морфолино-замещенные производные мочевины или карбамата в качестве ингибиторов mtor Download PDFInfo
- Publication number
- RU2616619C2 RU2616619C2 RU2014109747A RU2014109747A RU2616619C2 RU 2616619 C2 RU2616619 C2 RU 2616619C2 RU 2014109747 A RU2014109747 A RU 2014109747A RU 2014109747 A RU2014109747 A RU 2014109747A RU 2616619 C2 RU2616619 C2 RU 2616619C2
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- triazin
- methylsulfonyl
- urea
- methylmorpholino
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- 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
-
- 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
- A61P37/04—Immunostimulants
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11182221 | 2011-09-21 | ||
| EP11182221.9 | 2011-09-21 | ||
| PCT/EP2012/068590 WO2013041652A1 (en) | 2011-09-21 | 2012-09-21 | Morpholino substituted urea or carbamate derivatives as mtor inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2014109747A RU2014109747A (ru) | 2015-10-27 |
| RU2616619C2 true RU2616619C2 (ru) | 2017-04-18 |
Family
ID=46881066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014109747A RU2616619C2 (ru) | 2011-09-21 | 2012-09-21 | Морфолино-замещенные производные мочевины или карбамата в качестве ингибиторов mtor |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9175011B2 (enExample) |
| EP (1) | EP2758379B1 (enExample) |
| JP (1) | JP5995975B2 (enExample) |
| KR (1) | KR20140070616A (enExample) |
| CN (1) | CN103917530B (enExample) |
| AU (1) | AU2012311458B2 (enExample) |
| BR (1) | BR112014006743A8 (enExample) |
| CA (1) | CA2849189A1 (enExample) |
| ES (1) | ES2609606T3 (enExample) |
| RU (1) | RU2616619C2 (enExample) |
| WO (1) | WO2013041652A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2542536B1 (en) | 2010-03-04 | 2015-01-21 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
| MX341577B (es) | 2011-10-07 | 2016-08-25 | Cellzome Ltd | Derivados biciclicos de pirimidin-urea o carbamato sustituidos con morfolino como inhibidores del blanco de rapamicina de mamifero. |
| US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
| CN109715163B (zh) | 2016-09-19 | 2022-11-22 | 诺华股份有限公司 | 包含raf抑制剂和erk抑制剂的治疗组合 |
| WO2018203219A1 (en) | 2017-05-02 | 2018-11-08 | Novartis Ag | Combination therapy |
| AU2019338207B2 (en) | 2018-09-10 | 2025-01-02 | Mirati Therapeutics, Inc. | Combination therapies |
| EP4563150A3 (en) | 2019-05-13 | 2025-07-23 | Novartis AG | New crystalline forms of n-(3-(2-(2-hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methvlphenyl)-2(trifluoromethyl) isonicotinamide as raf inhibitors for the treatment of cancer |
| US12576069B2 (en) | 2019-09-11 | 2026-03-17 | Yale University | Compositions and methods for treating slow-flow vascular malformations |
| CN115109049B (zh) * | 2022-08-12 | 2023-08-15 | 江西科技师范大学 | 含芳基脲结构的三嗪类化合物及其应用 |
| GB202415232D0 (en) | 2024-10-16 | 2024-11-27 | Nacamed As | Composition |
| WO2026092678A1 (zh) * | 2024-11-01 | 2026-05-07 | 上海翰森生物医药科技有限公司 | 芳香胺类衍生物抑制剂、其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009143313A1 (en) * | 2008-05-23 | 2009-11-26 | Wyeth | Triazine compounds as p13 kinase and mtor inhibitors |
| RU2009110255A (ru) * | 2006-08-24 | 2010-09-27 | Астразенека Аб (Se) | Производные морфолинопиримидина, полезные для лечения пролиферативных нарушений |
| WO2011107585A1 (en) * | 2010-03-04 | 2011-09-09 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2284200T3 (es) | 1997-02-12 | 2007-11-01 | Electrophoretics Limited | Marcadores proteicos para cancer de pulmon y uso de los mismos. |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| ATE401312T1 (de) | 1997-12-15 | 2008-08-15 | Astellas Pharma Inc | Pyrimidin-5-carboxamid-derivate |
| EE05345B1 (et) | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Kinasoliini derivaadid angiogeneesi inhibiitoritena |
| PT1244647E (pt) | 1999-11-05 | 2006-10-31 | Astrazeneca Ab | Derivados de quinazolina como inibidores de vegf |
| HRP20020751B1 (hr) | 2000-02-15 | 2011-01-31 | Sugen | Pirolom supstituirani 2-indolinoni kao inhibitori protein kinaze |
| US7135298B2 (en) | 2003-03-26 | 2006-11-14 | The Burnham Institute For Medical Research | Screening assay for agents that alter target of Rapamycin activity |
| JP2008540391A (ja) | 2005-05-05 | 2008-11-20 | アストラゼネカ アクチボラグ | ピラゾリルアミノ置換ピリミジン、および癌の処置におけるそれらの使用 |
| PL1891446T3 (pl) | 2005-06-14 | 2013-08-30 | Cellzome Gmbh | Sposób identyfikacji nowych związków oddziałujących z enzymami |
| ES2317382T3 (es) | 2006-08-03 | 2009-04-16 | Cellzome Ag | Metodos para la identificacion de moleculas que interactuan con p13k y para la purificacion p13k. |
| WO2008023159A1 (en) | 2006-08-24 | 2008-02-28 | Astrazeneca Ab | Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders |
| US20080234262A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| US20080233127A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| US8012986B2 (en) * | 2007-04-02 | 2011-09-06 | Hoffmann-La Roche Inc. | Pyridine and pyrimidine derivatives as MGLUR2 antagonists |
| DK2146779T3 (en) | 2007-04-18 | 2016-11-28 | Pfizer Prod Inc | Sulfonylamid derivatives to treat abnormal cell growth. |
| WO2009008992A2 (en) | 2007-07-06 | 2009-01-15 | Osi Pharmaceuticals Inc. | Combination anti-cancer therapy comprising an inhibitor of both mtorc1 and mt0rc2 |
| JP2010533159A (ja) | 2007-07-09 | 2010-10-21 | アストラゼネカ アクチボラグ | 化合物９４７ |
| JP2010533158A (ja) | 2007-07-09 | 2010-10-21 | アストラゼネカ アクチボラグ | 化合物類−９４５ |
| JP2010533161A (ja) | 2007-07-09 | 2010-10-21 | アストラゼネカ アクチボラグ | 化合物−９４６ |
| WO2009007750A1 (en) | 2007-07-09 | 2009-01-15 | Astrazeneca Ab | Morpholino pyrimidine derivatives used in diseases linked to mtor kinase and/or pi3k |
| CN101224207A (zh) | 2007-10-12 | 2008-07-23 | 中国科学院上海有机化学研究所 | 具有诱导自吞噬治疗错误折叠蛋白聚集所致疾病的药物及其筛选方法 |
| WO2009093981A1 (en) * | 2008-01-23 | 2009-07-30 | S Bio Pte Ltd | Triazine compounds as kinase inhibitors |
| EP2410062A1 (en) | 2008-02-04 | 2012-01-25 | Cellzome Ag | Selectivity profiling of PI3K interacting molecules against multiple targets |
| US8163763B2 (en) | 2008-07-31 | 2012-04-24 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
| GB2465405A (en) | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| WO2010096619A1 (en) | 2009-02-23 | 2010-08-26 | Wyeth Llc | Process, purification and crystallization of 1-(4-{[4-(dimethylamino)piperidin-1-yl]carbonyl}phenyl)-3-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]urea |
| WO2010103094A1 (en) | 2009-03-13 | 2010-09-16 | Cellzome Limited | PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
| WO2010120994A2 (en) | 2009-04-17 | 2010-10-21 | Wyeth Llc | Ureidoaryl-and carbamoylaryl-morpholino- pyrimidine compounds, their use as mtor kinase and pi3 kinase inhibitors, and their synthesis |
| ES2439793T3 (es) | 2009-04-17 | 2014-01-24 | Wyeth Llc | Compuestos de pirimidina, su uso como inhibidores de la mTOR quinasa y de la PI3 quinasa, y su síntesis |
| WO2011011716A1 (en) | 2009-07-23 | 2011-01-27 | The Trustees Of Princeton University | Inhibitors of mtor kinase as anti-viral agents |
| US20140163023A1 (en) | 2011-04-04 | 2014-06-12 | Cellzome Limited | Dihydropyrrolo pyrimidine derivatives as mtor inhibitors |
| MX341577B (es) | 2011-10-07 | 2016-08-25 | Cellzome Ltd | Derivados biciclicos de pirimidin-urea o carbamato sustituidos con morfolino como inhibidores del blanco de rapamicina de mamifero. |
-
2012
- 2012-09-21 BR BR112014006743A patent/BR112014006743A8/pt not_active Application Discontinuation
- 2012-09-21 KR KR1020147010624A patent/KR20140070616A/ko not_active Ceased
- 2012-09-21 EP EP12761738.9A patent/EP2758379B1/en active Active
- 2012-09-21 WO PCT/EP2012/068590 patent/WO2013041652A1/en not_active Ceased
- 2012-09-21 AU AU2012311458A patent/AU2012311458B2/en not_active Ceased
- 2012-09-21 US US14/346,332 patent/US9175011B2/en not_active Expired - Fee Related
- 2012-09-21 ES ES12761738.9T patent/ES2609606T3/es active Active
- 2012-09-21 RU RU2014109747A patent/RU2616619C2/ru not_active IP Right Cessation
- 2012-09-21 CN CN201280055609.8A patent/CN103917530B/zh not_active Expired - Fee Related
- 2012-09-21 CA CA2849189A patent/CA2849189A1/en not_active Abandoned
- 2012-09-21 JP JP2014531240A patent/JP5995975B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2009110255A (ru) * | 2006-08-24 | 2010-09-27 | Астразенека Аб (Se) | Производные морфолинопиримидина, полезные для лечения пролиферативных нарушений |
| WO2009143313A1 (en) * | 2008-05-23 | 2009-11-26 | Wyeth | Triazine compounds as p13 kinase and mtor inhibitors |
| WO2011107585A1 (en) * | 2010-03-04 | 2011-09-09 | Cellzome Limited | Morpholino substituted urea derivatives as mtor inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014006743A8 (pt) | 2018-01-09 |
| EP2758379A1 (en) | 2014-07-30 |
| BR112014006743A2 (pt) | 2017-04-11 |
| CA2849189A1 (en) | 2013-03-28 |
| US9175011B2 (en) | 2015-11-03 |
| AU2012311458A1 (en) | 2014-04-10 |
| JP2014530197A (ja) | 2014-11-17 |
| US20140378438A1 (en) | 2014-12-25 |
| WO2013041652A1 (en) | 2013-03-28 |
| ES2609606T3 (es) | 2017-04-21 |
| JP5995975B2 (ja) | 2016-09-21 |
| RU2014109747A (ru) | 2015-10-27 |
| EP2758379B1 (en) | 2016-10-19 |
| AU2012311458B2 (en) | 2016-02-04 |
| CN103917530B (zh) | 2016-08-24 |
| CN103917530A (zh) | 2014-07-09 |
| KR20140070616A (ko) | 2014-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20190922 |