AU2014318979B2 - Sodium channel modulators for the treatment of pain and diabetes - Google Patents
Sodium channel modulators for the treatment of pain and diabetes Download PDFInfo
- Publication number
- AU2014318979B2 AU2014318979B2 AU2014318979A AU2014318979A AU2014318979B2 AU 2014318979 B2 AU2014318979 B2 AU 2014318979B2 AU 2014318979 A AU2014318979 A AU 2014318979A AU 2014318979 A AU2014318979 A AU 2014318979A AU 2014318979 B2 AU2014318979 B2 AU 2014318979B2
- Authority
- AU
- Australia
- Prior art keywords
- chloro
- propyl
- formula
- sulfamoyl
- thiazol
- 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.)
- Ceased
Links
- OPTCHSMAUQAOEX-UHFFFAOYSA-N CCC(O1)=C(C)OC1=O Chemical compound CCC(O1)=C(C)OC1=O OPTCHSMAUQAOEX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0021—Intradermal administration, e.g. through microneedle arrays or needleless injectors
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361876046P | 2013-09-10 | 2013-09-10 | |
| US61/876,046 | 2013-09-10 | ||
| PCT/US2014/054764 WO2015038533A2 (en) | 2013-09-10 | 2014-09-09 | Sodium channel modulators for the treatment of pain and diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014318979A1 AU2014318979A1 (en) | 2016-03-03 |
| AU2014318979B2 true AU2014318979B2 (en) | 2019-03-28 |
Family
ID=52666496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014318979A Ceased AU2014318979B2 (en) | 2013-09-10 | 2014-09-09 | Sodium channel modulators for the treatment of pain and diabetes |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20160221974A1 (enExample) |
| EP (1) | EP3043787B1 (enExample) |
| JP (1) | JP6445565B2 (enExample) |
| KR (1) | KR20160054570A (enExample) |
| CN (1) | CN105611923B (enExample) |
| AU (1) | AU2014318979B2 (enExample) |
| BR (1) | BR112016005271A2 (enExample) |
| CA (1) | CA2922851C (enExample) |
| ES (1) | ES2687598T3 (enExample) |
| IL (1) | IL244506B (enExample) |
| MX (1) | MX2016002881A (enExample) |
| MY (1) | MY181928A (enExample) |
| PH (1) | PH12016500296A1 (enExample) |
| RU (1) | RU2016113156A (enExample) |
| SG (2) | SG10201805552PA (enExample) |
| UA (1) | UA120353C2 (enExample) |
| WO (1) | WO2015038533A2 (enExample) |
| ZA (1) | ZA201702410B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10179781B2 (en) * | 2013-03-15 | 2019-01-15 | Chromocell Corporation | Sodium channel modulators for the treatment of pain |
| CN105611923B (zh) | 2013-09-10 | 2019-08-23 | 卓莫赛尔公司 | 用于治疗疼痛和糖尿病的钠通道调节剂 |
| EP3193610A4 (en) * | 2014-09-09 | 2018-04-04 | Chromocell Corporation | Selective nav1.7 inhibitors for the treatment of diabetes |
| CN108699015A (zh) | 2015-12-18 | 2018-10-23 | 默沙东公司 | 对电压门控性钠通道具有选择性活性的羟基烷基胺-和羟基环烷基胺-取代的二胺-芳基磺胺化合物 |
| WO2017201468A1 (en) | 2016-05-20 | 2017-11-23 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| CN105924670A (zh) * | 2016-06-02 | 2016-09-07 | 扬州兰都塑料科技有限公司 | 一种电力电缆用耐磨剂 |
| CN105924843A (zh) * | 2016-06-02 | 2016-09-07 | 扬州兰都塑料科技有限公司 | 一种耐刮擦的电力电缆 |
| CN106084535A (zh) * | 2016-06-02 | 2016-11-09 | 扬州兰都塑料科技有限公司 | 一种耐刮擦的电力电缆的制备方法 |
| EP3551626B1 (en) | 2016-12-09 | 2023-10-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| CN106892845B (zh) * | 2017-02-28 | 2018-10-30 | 四川同晟生物医药有限公司 | 一种2,4-二氨基丁酸衍生物及其制备方法 |
| WO2019200369A1 (en) * | 2018-04-13 | 2019-10-17 | Chromocell Corporation | Compounds and methods of using compounds for the prevention or treatment of peripheral nerve damage |
| WO2019217822A1 (en) * | 2018-05-11 | 2019-11-14 | Chromocell Corporation | Compounds and methods of using compounds for the prevention or treatment of inflammatory conditions |
| AU2019285184B2 (en) | 2018-06-13 | 2023-11-16 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| MA53488A (fr) | 2018-08-31 | 2021-12-08 | Xenon Pharmaceuticals Inc | Composés de sulfonamide substitués par hétéroaryle et leur utilisation en tant qu'inhibiteurs de canaux sodiques |
| US10981905B2 (en) | 2018-08-31 | 2021-04-20 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as therapeutic agents |
| CN113527281B (zh) * | 2020-04-20 | 2023-12-22 | 昆山彭济凯丰生物科技有限公司 | 杂环化合物及其制备方法和应用 |
| WO2026090267A1 (en) * | 2024-10-23 | 2026-04-30 | Pelthos Therapeutics Inc. | Ophthalmic formulations |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100197655A1 (en) * | 2009-01-12 | 2010-08-05 | Pfizer Limited Icagen, Inc. | Sulfonamide derivatives |
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| US5356897A (en) | 1991-09-09 | 1994-10-18 | Fujisawa Pharmaceutical Co., Ltd. | 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines |
| PT1368355E (pt) * | 2001-03-14 | 2006-09-29 | Gruenenthal Gmbh | Pirazolopirimidinas e tiazolopirimidinas substituidas, como analgesicos |
| US7659082B2 (en) | 2002-02-19 | 2010-02-09 | Xenon Pharmaceuticals Inc. | Methods for identifying analgesic agents |
| CA2744893A1 (en) | 2002-06-27 | 2004-01-08 | Novo Nordisk A/S | Aryl carbonyl derivatives as glucokinase activators |
| GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
| EP1689719A1 (en) | 2003-11-25 | 2006-08-16 | Eli Lilly And Company | 7-phenyl-isoquinoline-5-sulfonylamino derivatives as inhibitors of akt (proteinkinase b) |
| EP1751136B1 (en) | 2004-05-07 | 2014-07-02 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
| WO2006011050A2 (en) * | 2004-07-23 | 2006-02-02 | Pfizer Limited | Pyridine derivatives |
| WO2006046916A1 (en) | 2004-10-29 | 2006-05-04 | Astrazeneca Ab | Novel sulphonamide derivatives as glucocorticoid receptor modulators for the treatment of inflammatory diseases |
| US7622496B2 (en) * | 2005-12-23 | 2009-11-24 | Zealand Pharma A/S | Modified lysine-mimetic compounds |
| CA2677493A1 (en) * | 2007-02-05 | 2008-08-14 | Xenon Pharmaceuticals Inc. | Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions |
| JP5460589B2 (ja) | 2007-07-13 | 2014-04-02 | アイカジェン, インコーポレイテッド | ナトリウムチャネル阻害物質 |
| US8853250B2 (en) | 2007-07-13 | 2014-10-07 | Icagen, Inc. | Sodium channel inhibitors |
| KR101605061B1 (ko) | 2009-05-29 | 2016-03-21 | 라퀄리아 파마 인코포레이티드 | 칼슘 또는 나트륨 채널 차단제로서의 아릴 치환된 카복사미드 유도체 |
| EP2560636A4 (en) | 2010-04-23 | 2013-11-27 | Kineta Inc | ANTIVIRAL CONNECTIONS |
| WO2012004743A1 (en) | 2010-07-09 | 2012-01-12 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| JP5872552B2 (ja) | 2010-07-09 | 2016-03-01 | ファイザー・リミテッドPfizer Limited | 化学化合物 |
| ES2526675T3 (es) | 2010-07-09 | 2015-01-14 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de los canales de sodio dependientes de voltaje |
| EP2593427B1 (en) | 2010-07-12 | 2014-12-24 | Pfizer Limited | Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain |
| WO2012099983A1 (en) | 2011-01-18 | 2012-07-26 | Amgen Inc. | Nav1.7 knockout mice and uses thereof |
| UY34171A (es) * | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| AU2012296529A1 (en) | 2011-08-17 | 2014-02-20 | Amgen Inc. | Heteroaryl sodium channel inhibitors |
| WO2013043925A1 (en) * | 2011-09-21 | 2013-03-28 | Gilead Sciences, Inc. | Sodium channel blockers reduce glucagon secretion |
| MX2014005304A (es) | 2011-10-31 | 2015-03-20 | Xenon Pharmaceuticals Inc | Biaril eter sulfonamidas y su uso como agentes terapeuticos. |
| US9757379B2 (en) | 2012-11-14 | 2017-09-12 | The Board Of Regents Of The University Of Texas System | Inhibition of HIF-2α heterodimerization with HIF1β (ARNT) |
| US10179781B2 (en) * | 2013-03-15 | 2019-01-15 | Chromocell Corporation | Sodium channel modulators for the treatment of pain |
| EP3417851B1 (en) | 2013-09-09 | 2020-07-22 | Peloton Therapeutics, Inc. | Aryl ethers and uses thereof |
| CN105611923B (zh) | 2013-09-10 | 2019-08-23 | 卓莫赛尔公司 | 用于治疗疼痛和糖尿病的钠通道调节剂 |
| EP3193610A4 (en) | 2014-09-09 | 2018-04-04 | Chromocell Corporation | Selective nav1.7 inhibitors for the treatment of diabetes |
-
2014
- 2014-09-09 CN CN201480049690.8A patent/CN105611923B/zh not_active Expired - Fee Related
- 2014-09-09 US US15/021,153 patent/US20160221974A1/en not_active Abandoned
- 2014-09-09 RU RU2016113156A patent/RU2016113156A/ru not_active Application Discontinuation
- 2014-09-09 SG SG10201805552PA patent/SG10201805552PA/en unknown
- 2014-09-09 BR BR112016005271-4A patent/BR112016005271A2/pt not_active IP Right Cessation
- 2014-09-09 SG SG11201601367QA patent/SG11201601367QA/en unknown
- 2014-09-09 KR KR1020167009294A patent/KR20160054570A/ko not_active Ceased
- 2014-09-09 MX MX2016002881A patent/MX2016002881A/es active IP Right Grant
- 2014-09-09 UA UAA201603676A patent/UA120353C2/uk unknown
- 2014-09-09 ES ES14843353.5T patent/ES2687598T3/es active Active
- 2014-09-09 JP JP2016540921A patent/JP6445565B2/ja active Active
- 2014-09-09 AU AU2014318979A patent/AU2014318979B2/en not_active Ceased
- 2014-09-09 WO PCT/US2014/054764 patent/WO2015038533A2/en not_active Ceased
- 2014-09-09 MY MYPI2016700824A patent/MY181928A/en unknown
- 2014-09-09 CA CA2922851A patent/CA2922851C/en active Active
- 2014-09-09 EP EP14843353.5A patent/EP3043787B1/en active Active
-
2016
- 2016-01-13 US US14/994,846 patent/US9458118B2/en active Active
- 2016-02-12 PH PH12016500296A patent/PH12016500296A1/en unknown
- 2016-03-09 IL IL244506A patent/IL244506B/en active IP Right Grant
-
2017
- 2017-04-05 ZA ZA2017/02410A patent/ZA201702410B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100197655A1 (en) * | 2009-01-12 | 2010-08-05 | Pfizer Limited Icagen, Inc. | Sulfonamide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2922851C (en) | 2023-03-14 |
| RU2016113156A (ru) | 2017-10-16 |
| ES2687598T3 (es) | 2018-10-26 |
| CN105611923B (zh) | 2019-08-23 |
| CA2922851A1 (en) | 2015-03-19 |
| EP3043787A4 (en) | 2017-02-01 |
| CN105611923A (zh) | 2016-05-25 |
| US20160221974A1 (en) | 2016-08-04 |
| RU2016113156A3 (enExample) | 2018-07-02 |
| WO2015038533A3 (en) | 2015-10-29 |
| KR20160054570A (ko) | 2016-05-16 |
| EP3043787B1 (en) | 2018-09-05 |
| US9458118B2 (en) | 2016-10-04 |
| UA120353C2 (uk) | 2019-11-25 |
| PH12016500296A1 (en) | 2016-05-16 |
| US20160130239A1 (en) | 2016-05-12 |
| SG10201805552PA (en) | 2018-08-30 |
| SG11201601367QA (en) | 2016-03-30 |
| IL244506A0 (en) | 2016-04-21 |
| JP6445565B2 (ja) | 2018-12-26 |
| BR112016005271A2 (pt) | 2020-05-12 |
| MY181928A (en) | 2021-01-14 |
| AU2014318979A1 (en) | 2016-03-03 |
| ZA201702410B (en) | 2019-06-26 |
| WO2015038533A2 (en) | 2015-03-19 |
| JP2016532716A (ja) | 2016-10-20 |
| EP3043787A2 (en) | 2016-07-20 |
| MX2016002881A (es) | 2016-04-21 |
| IL244506B (en) | 2020-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |