CN106632243B - 吡咯烷衍生物 - Google Patents

吡咯烷衍生物 Download PDF

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Publication number
CN106632243B
CN106632243B CN201510713865.7A CN201510713865A CN106632243B CN 106632243 B CN106632243 B CN 106632243B CN 201510713865 A CN201510713865 A CN 201510713865A CN 106632243 B CN106632243 B CN 106632243B
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CN
China
Prior art keywords
azabicyclo
ylethynyl
pyridin
compound
hex
Prior art date
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Application number
CN201510713865.7A
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English (en)
Chinese (zh)
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CN106632243A (zh
Inventor
陈力
段月姣
吴成德
沈春莉
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Hua Medicine Shanghai Ltd
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Hua Medicine Shanghai Ltd
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.)
Filing date
Publication date
Priority to CN201510713865.7A priority Critical patent/CN106632243B/zh
Application filed by Hua Medicine Shanghai Ltd filed Critical Hua Medicine Shanghai Ltd
Priority to PCT/CN2016/102946 priority patent/WO2017071536A1/en
Priority to KR1020187014851A priority patent/KR102815874B1/ko
Priority to JP2018541471A priority patent/JP6877771B2/ja
Priority to ES16858971T priority patent/ES2922978T3/es
Priority to HUE16858971A priority patent/HUE058899T2/hu
Priority to RU2018119038A priority patent/RU2740019C1/ru
Priority to AU2016345244A priority patent/AU2016345244B2/en
Priority to MX2018004868A priority patent/MX385587B/es
Priority to HK18113542.6A priority patent/HK1254456B/en
Priority to DK16858971.1T priority patent/DK3371163T3/da
Priority to CA3000794A priority patent/CA3000794C/en
Priority to CN201680062993.2A priority patent/CN108349935B/zh
Priority to US15/771,920 priority patent/US10328054B2/en
Priority to BR112018008204-0A priority patent/BR112018008204B1/pt
Priority to EP16858971.1A priority patent/EP3371163B1/en
Priority to TW105134694A priority patent/TWI725998B/zh
Publication of CN106632243A publication Critical patent/CN106632243A/zh
Priority to ZA2018/02235A priority patent/ZA201802235B/en
Priority to IL258517A priority patent/IL258517B/en
Application granted granted Critical
Publication of CN106632243B publication Critical patent/CN106632243B/zh
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    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/495—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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61P25/28—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
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/08—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 carbon chain containing alicyclic 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
    • C07D401/14—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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CN201510713865.7A 2015-10-28 2015-10-28 吡咯烷衍生物 Active CN106632243B (zh)

Priority Applications (19)

Application Number Priority Date Filing Date Title
CN201510713865.7A CN106632243B (zh) 2015-10-28 2015-10-28 吡咯烷衍生物
CA3000794A CA3000794C (en) 2015-10-28 2016-10-21 Pyrrolidine derivatives
JP2018541471A JP6877771B2 (ja) 2015-10-28 2016-10-21 ピロリジン誘導体
ES16858971T ES2922978T3 (es) 2015-10-28 2016-10-21 Derivados de pirrolidina
HUE16858971A HUE058899T2 (hu) 2015-10-28 2016-10-21 Pirrolidinszármazékok
RU2018119038A RU2740019C1 (ru) 2015-10-28 2016-10-21 Производные пирролидина
AU2016345244A AU2016345244B2 (en) 2015-10-28 2016-10-21 Pyrrolidine derivatives
US15/771,920 US10328054B2 (en) 2015-10-28 2016-10-21 Substituted pyrrolidines as mGluR5 antagonists
KR1020187014851A KR102815874B1 (ko) 2015-10-28 2016-10-21 피롤리딘 유도체
DK16858971.1T DK3371163T3 (da) 2015-10-28 2016-10-21 Pyrrolidinderivater
PCT/CN2016/102946 WO2017071536A1 (en) 2015-10-28 2016-10-21 Pyrrolidine derivatives
HK18113542.6A HK1254456B (en) 2015-10-28 2016-10-21 Pyrrolidine derivatives
MX2018004868A MX385587B (es) 2015-10-28 2016-10-21 Derivados de la pirrolidina.
BR112018008204-0A BR112018008204B1 (pt) 2015-10-28 2016-10-21 Composto, composição farmacêutica, e, método para tratamento de distúrbios associados com irregularidades da transmissão de sinal glutamatérgico e de distúrbios do sistema nervoso central
EP16858971.1A EP3371163B1 (en) 2015-10-28 2016-10-21 Pyrrolidine derivatives
CN201680062993.2A CN108349935B (zh) 2015-10-28 2016-10-21 吡咯烷衍生物
TW105134694A TWI725998B (zh) 2015-10-28 2016-10-27 化合物或其可藥用鹽、藥物組合物及其用途
ZA2018/02235A ZA201802235B (en) 2015-10-28 2018-04-05 Pyrrolidine derivatives
IL258517A IL258517B (en) 2015-10-28 2018-04-05 History of pyrrolidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510713865.7A CN106632243B (zh) 2015-10-28 2015-10-28 吡咯烷衍生物

Publications (2)

Publication Number Publication Date
CN106632243A CN106632243A (zh) 2017-05-10
CN106632243B true CN106632243B (zh) 2019-03-15

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CN201510713865.7A Active CN106632243B (zh) 2015-10-28 2015-10-28 吡咯烷衍生物
CN201680062993.2A Active CN108349935B (zh) 2015-10-28 2016-10-21 吡咯烷衍生物

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN201680062993.2A Active CN108349935B (zh) 2015-10-28 2016-10-21 吡咯烷衍生物

Country Status (17)

Country Link
US (1) US10328054B2 (enExample)
EP (1) EP3371163B1 (enExample)
JP (1) JP6877771B2 (enExample)
KR (1) KR102815874B1 (enExample)
CN (2) CN106632243B (enExample)
AU (1) AU2016345244B2 (enExample)
BR (1) BR112018008204B1 (enExample)
CA (1) CA3000794C (enExample)
DK (1) DK3371163T3 (enExample)
ES (1) ES2922978T3 (enExample)
HU (1) HUE058899T2 (enExample)
IL (1) IL258517B (enExample)
MX (1) MX385587B (enExample)
RU (1) RU2740019C1 (enExample)
TW (1) TWI725998B (enExample)
WO (1) WO2017071536A1 (enExample)
ZA (1) ZA201802235B (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015051244A1 (en) 2013-10-04 2015-04-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
EP3119397B1 (en) 2014-03-19 2022-03-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders
CN114230571B (zh) 2015-09-14 2025-07-08 无限药品股份有限公司 异喹啉酮的固体形式、其制备方法、包含其的组合物及其使用方法
CN106632243B (zh) * 2015-10-28 2019-03-15 华领医药技术（上海）有限公司 吡咯烷衍生物
KR102740618B1 (ko) * 2021-11-17 2024-12-10 유노비아 주식회사 아이속사졸 유도체의 제조 방법 및 그의 중간체
CN119569744A (zh) * 2024-11-19 2025-03-07 武汉大学人民医院（湖北省人民医院） 吡喃吡啶酮生物碱类化合物及其制备方法和应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0503646D0 (en) * 2005-02-22 2005-03-30 Novartis Ag Organic compounds
CN101990536B (zh) * 2008-01-18 2014-09-03 上海靶点药物有限公司 基于吡咯烷的化合物
TW201116532A (en) * 2009-08-05 2011-05-16 Merz Pharma Gmbh & Co Kgaa Metabotropic glutamate receptor modulators
US8420661B2 (en) * 2010-04-13 2013-04-16 Hoffmann-La Roche Inc. Arylethynyl derivatives
WO2012152854A1 (en) * 2011-05-12 2012-11-15 Merz Pharma Gmbh & Co. Kgaa Metabotropic glutamate receptor modulators
UA110862C2 (uk) * 2011-10-07 2016-02-25 Ф. Хоффманн-Ля Рош Аг Похідні етинілу як алостеричні модулятори метаботропного рецептора глутамату mglur 5
WO2014124560A1 (en) * 2013-02-18 2014-08-21 Hua Medicine (Shanghai) Ltd. Mglur regulators
CN106632243B (zh) * 2015-10-28 2019-03-15 华领医药技术（上海）有限公司 吡咯烷衍生物

Also Published As

Publication number Publication date
DK3371163T3 (da) 2022-07-04
KR102815874B1 (ko) 2025-06-02
EP3371163B1 (en) 2022-03-30
RU2740019C1 (ru) 2020-12-30
IL258517B (en) 2020-05-31
EP3371163A1 (en) 2018-09-12
KR20180070693A (ko) 2018-06-26
IL258517A (en) 2018-05-31
JP2018532778A (ja) 2018-11-08
US10328054B2 (en) 2019-06-25
EP3371163A4 (en) 2019-05-01
BR112018008204A2 (pt) 2018-12-18
AU2016345244B2 (en) 2020-07-09
ES2922978T3 (es) 2022-09-22
CA3000794C (en) 2024-01-16
US20180318254A1 (en) 2018-11-08
CN106632243A (zh) 2017-05-10
CN108349935B (zh) 2021-02-05
HK1254456A1 (en) 2019-07-19
TW201718542A (zh) 2017-06-01
CN108349935A (zh) 2018-07-31
MX385587B (es) 2025-03-18
MX2018004868A (es) 2018-11-09
WO2017071536A1 (en) 2017-05-04
HUE058899T2 (hu) 2022-09-28
BR112018008204B1 (pt) 2023-12-26
CA3000794A1 (en) 2017-05-04
AU2016345244A1 (en) 2018-04-26
TWI725998B (zh) 2021-05-01
JP6877771B2 (ja) 2021-05-26
ZA201802235B (en) 2019-07-31

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