PL3434669T3 - Związki pośrednie mające zastosowanie w syntezie (-)-hupercyny i sposób otrzymywania jednego z tych związków pośrednich - Google Patents

Związki pośrednie mające zastosowanie w syntezie (-)-hupercyny i sposób otrzymywania jednego z tych związków pośrednich

Info

Publication number: PL3434669T3
Authority: PL; Poland
Prior art keywords: intermediate compounds; huperzine; synthesis; utilizable; compounds utilizable
Prior art date: 2011-03-04

Application number

PL18188873T

Other languages

English (en)

Inventor

Seth HERZON

Maung Kway Moe Tun

Original Assignee

Yale University

Priority date (The priority date 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 date listed.)

2011-03-04

Filing date

2012-02-17

Publication date

2021-05-31

2012-02-17 Application filed by Yale University filed Critical Yale University

2021-05-31 Publication of PL3434669T3 publication Critical patent/PL3434669T3/pl

Links

150000001875 compounds Chemical class 0.000 title 2
ZQPQGKQTIZYFEF-WCVJEAGWSA-N Huperzine Natural products C1([C@H]2[C@H](O)C(=O)N[C@H]2[C@@H](O)C=2C=CC=CC=2)=CC=CC=C1 ZQPQGKQTIZYFEF-WCVJEAGWSA-N 0.000 title 1
230000015572 biosynthetic process Effects 0.000 title 1
238000000034 method Methods 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
- 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
- A61K31/4748—Quinolines; Isoquinolines forming part of bridged ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Diabetes (AREA)
Addiction (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Psychology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Toxicology (AREA)
Obesity (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)

PL18188873T 2011-03-04 2012-02-17 Związki pośrednie mające zastosowanie w syntezie (-)-hupercyny i sposób otrzymywania jednego z tych związków pośrednich PL3434669T3 (pl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US201161449198P	2011-03-04	2011-03-04
EP12755750.2A EP2681199B1 (en)	2011-03-04	2012-02-17	Process for the preparation of (-)-huperzine a
EP18188873.6A EP3434669B1 (en)	2011-03-04	2012-02-17	Intermediate compounds utilizable in synthesis of (-) huperzine and process for obtain one of these intermediate compounds
PCT/US2012/025628 WO2012121863A1 (en)	2011-03-04	2012-02-17	(--)- huperzine a processes and related compositions and methods of treatment

Publications (1)

Publication Number	Publication Date
PL3434669T3 true PL3434669T3 (pl)	2021-05-31

Family

ID=46798513

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
PL12755750T PL2681199T3 (pl)	2011-03-04	2012-02-17	Sposób wytwarzania (-)-hupercyny A
PL18188873T PL3434669T3 (pl)	2011-03-04	2012-02-17	Związki pośrednie mające zastosowanie w syntezie (-)-hupercyny i sposób otrzymywania jednego z tych związków pośrednich

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
PL12755750T PL2681199T3 (pl)	2011-03-04	2012-02-17	Sposób wytwarzania (-)-hupercyny A

Country Status (11)

Country	Link
US (5)	US10059672B2 (pl)
EP (2)	EP3434669B1 (pl)
JP (2)	JP5922157B2 (pl)
KR (1)	KR102017123B1 (pl)
CN (2)	CN106117140B (pl)
AU (2)	AU2012226251B2 (pl)
CA (1)	CA2829026C (pl)
ES (2)	ES2701730T3 (pl)
MX (2)	MX346339B (pl)
PL (2)	PL2681199T3 (pl)
WO (1)	WO2012121863A1 (pl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10287249B2 (en)	2014-10-03	2019-05-14	Amphastar Pharmaceuticals, Inc.	Methods of resolving racemic mixture to obtain (−)-huperzine A
ES2982382T3 (es) *	2017-05-19	2024-10-15	Biscayne Neurotherapeutics Inc	Composiciones farmacéuticas de liberación modificada de huperzina y procedimientos de utilización de las mismas
CN109200051A (zh) *	2017-07-03	2019-01-15	南京和博生物医药有限公司	石杉碱甲及其类似物作为治疗炎症性疾病药物的用途
AU2019384130B2 (en)	2018-11-19	2025-02-20	Supernus Pharmaceuticals, Inc.	Use of higher doses of modified release huperzine formulations
CN114702391B (zh) *	2021-12-17	2024-09-03	青岛科技大学	一种利用双氧水进行霍夫曼重排制环丙胺的方法

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US4522811A (en)	1982-07-08	1985-06-11	Syntex (U.S.A.) Inc.	Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides
US5104880A (en) *	1991-05-01	1992-04-14	Mayo Foundation For Medical Education And Research	Huperzine a analogs as acetylcholinesterase inhibitors
CN1052225C (zh) *	1994-12-28	2000-05-10	中国科学院上海药物研究所	石杉碱甲衍生物,其制备方法和用途
USRE38460E1 (en)	1994-12-28	2004-03-09	Shanghai Institute Of Materia Medica Chinese Academy Of Sciences	Huperzine A derivatives, their preparation and their use
JPH0995483A (ja) *	1995-07-27	1997-04-08	Sagami Chem Res Center	（１１Ｅ）−５−アミノ−１１−エチリデン−５，６，９，１０−テトラヒドロ−７−メチル−５，９−メタノシクロオクタ［ｂ］ピリジン−２（１Ｈ）−オン誘導体およびその製造中間体
JPH1036352A (ja) *	1996-07-23	1998-02-10	Sagami Chem Res Center	（１１Ｅ）−５−アミノ−１１−エチリデン−５，６，９，１０−テトラヒドロ−５，９−メタノシクロオクタ［ｂ］ピリジン−２（１Ｈ）−オン誘導体およびその製造中間体
WO1999011625A1 (en) *	1997-09-03	1999-03-11	Macro Hi-Tech Jv, Ltd.	Huperzine a derivatives
US6271397B1 (en)	1998-06-05	2001-08-07	Showa Denko Kabushiki Kaisha	L-ascorbic acid-2-phosphoric acid potassium crystal and method for producing the same
US6271379B1 (en) *	2000-03-08	2001-08-07	Georgetown University	Intermediates useful for the synthesis of huperzine A
CN1245386C (zh)	2000-06-12	2006-03-15	卫材株式会社	1,2－二氢吡啶化合物及其制备方法和用途
US8193212B2 (en) *	2005-05-23	2012-06-05	President And Fellows Of Harvard College	Use of huperzine for neuropathic pain
CN101130520B (zh) *	2006-08-24	2010-05-12	中国科学院上海药物研究所	经非对映异构体盐的外消旋体拆分制备天然(-)-石杉碱甲和非天然(+)-石杉碱甲的新方法
CN100528844C (zh) *	2007-04-20	2009-08-19	中国科学院昆明植物研究所	石杉碱甲衍生物,其制备方法和其应用
WO2009120774A2 (en) *	2008-03-25	2009-10-01	Debiopharm S.A.	Method of preparing huperzine a and derivatives thereof

2012
- 2012-02-17 MX MX2013010025A patent/MX346339B/es active IP Right Grant
- 2012-02-17 WO PCT/US2012/025628 patent/WO2012121863A1/en not_active Ceased
- 2012-02-17 PL PL12755750T patent/PL2681199T3/pl unknown
- 2012-02-17 EP EP18188873.6A patent/EP3434669B1/en active Active
- 2012-02-17 AU AU2012226251A patent/AU2012226251B2/en active Active
- 2012-02-17 CN CN201610463124.2A patent/CN106117140B/zh active Active
- 2012-02-17 EP EP12755750.2A patent/EP2681199B1/en active Active
- 2012-02-17 US US14/003,213 patent/US10059672B2/en active Active
- 2012-02-17 CN CN201280020578.2A patent/CN103687849B/zh active Active
- 2012-02-17 MX MX2017003129A patent/MX382066B/es unknown
- 2012-02-17 CA CA2829026A patent/CA2829026C/en active Active
- 2012-02-17 KR KR1020137026077A patent/KR102017123B1/ko active Active
- 2012-02-17 ES ES12755750T patent/ES2701730T3/es active Active
- 2012-02-17 PL PL18188873T patent/PL3434669T3/pl unknown
- 2012-02-17 ES ES18188873T patent/ES2847229T3/es active Active
- 2012-02-17 JP JP2013557736A patent/JP5922157B2/ja active Active
2016
- 2016-04-13 JP JP2016080553A patent/JP6200996B2/ja active Active
2017
- 2017-07-11 AU AU2017204748A patent/AU2017204748B2/en active Active
- 2017-12-20 US US15/848,350 patent/US10457643B2/en active Active
2019
- 2019-09-16 US US16/571,720 patent/US10781179B2/en active Active
2020
- 2020-06-04 US US16/892,828 patent/US11142503B2/en active Active
2021
- 2021-09-23 US US17/482,996 patent/US12134602B2/en active Active

Also Published As

Publication number	Publication date
EP3434669B1 (en)	2020-11-04
ES2701730T3 (es)	2019-02-25
US11142503B2 (en)	2021-10-12
PL2681199T3 (pl)	2019-03-29
WO2012121863A1 (en)	2012-09-13
CA2829026A1 (en)	2012-09-13
US10457643B2 (en)	2019-10-29
JP6200996B2 (ja)	2017-09-20
US20150158817A1 (en)	2015-06-11
CN106117140B (zh)	2020-05-05
JP5922157B2 (ja)	2016-05-24
MX2013010025A (es)	2014-03-27
MX382066B (es)	2025-03-12
ES2847229T3 (es)	2021-08-02
AU2012226251A1 (en)	2013-10-17
MX346339B (es)	2017-03-15
KR102017123B1 (ko)	2019-09-02
US20220064123A1 (en)	2022-03-03
AU2017204748A1 (en)	2017-07-27
EP2681199A1 (en)	2014-01-08
US10059672B2 (en)	2018-08-28
CA2829026C (en)	2020-08-11
EP3434669A1 (en)	2019-01-30
KR20140009444A (ko)	2014-01-22
JP2016185949A (ja)	2016-10-27
AU2012226251B2 (en)	2017-05-04
EP2681199B1 (en)	2018-09-26
JP2014508777A (ja)	2014-04-10
CN103687849B (zh)	2016-08-17
US20180237395A1 (en)	2018-08-23
CN103687849A (zh)	2014-03-26
US20200392086A1 (en)	2020-12-17
US12134602B2 (en)	2024-11-05
US10781179B2 (en)	2020-09-22
EP2681199A4 (en)	2014-08-06
CN106117140A (zh)	2016-11-16
US20200109118A1 (en)	2020-04-09
AU2017204748B2 (en)	2019-06-20

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