MA39855B1 - Nouveaux composés de succinate perméables à travers les cellules - Google Patents

Nouveaux composés de succinate perméables à travers les cellules

Info

Publication number
MA39855B1
MA39855B1 MA39855A MA39855A MA39855B1 MA 39855 B1 MA39855 B1 MA 39855B1 MA 39855 A MA39855 A MA 39855A MA 39855 A MA39855 A MA 39855A MA 39855 B1 MA39855 B1 MA 39855B1
Authority
MA
Morocco
Prior art keywords
cell
permeable
succinates
cells
atp
Prior art date
Application number
MA39855A
Other languages
English (en)
Other versions
MA39855A (fr
Inventor
Eskil Elmér
Magnus Joakim Hansson
Karl Henrik Johannes Ehinger
Steven Moss
Original Assignee
Neurovive Pharmaceutical Ab
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=58804197&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=MA39855(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Neurovive Pharmaceutical Ab filed Critical Neurovive Pharmaceutical Ab
Publication of MA39855A publication Critical patent/MA39855A/fr
Publication of MA39855B1 publication Critical patent/MA39855B1/fr

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Classifications

    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
    • 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
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C07C327/34—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups with amino groups bound to the same hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/18—Eight-membered rings
    • 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
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Cardiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

La présente invention concerne de nouveaux succinates perméables aux cellules et des précurseurs perméables aux cellules du succinate destinés à augmenter la production d'atp dans les mitochondries. La majeure partie de l'atp produite et utilisée dans la cellule eucaryote provient de la phosphorylation oxydative mitochondriale, processus auquel le cycle de kreb fournit des électrons de haute énergie. Tous les intermédiaires du cycle de kreb ne sont pas facilement perméables à la membrane cellulaire, l'un d'entre eux étant le succinate. La fourniture des nouveaux succinates perméables aux cellules est envisagée pour permettre le passage sur la membrane cellulaire et ainsi les succinates perméables aux cellules peuvent être utilisés pour améliorer la sortie d'atp mitochondrial.
MA39855A 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules MA39855B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DKPA201470190 2014-04-08
EP15714820.6A EP3129016B1 (fr) 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules
PCT/EP2015/057606 WO2015155231A1 (fr) 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules

Publications (2)

Publication Number Publication Date
MA39855A MA39855A (fr) 2018-10-24
MA39855B1 true MA39855B1 (fr) 2018-10-31

Family

ID=58804197

Family Applications (2)

Application Number Title Priority Date Filing Date
MA44092A MA44092B1 (fr) 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules
MA39855A MA39855B1 (fr) 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules

Family Applications Before (1)

Application Number Title Priority Date Filing Date
MA44092A MA44092B1 (fr) 2014-04-08 2015-04-08 Nouveaux composés de succinate perméables à travers les cellules

Country Status (25)

Country Link
US (2) US11147789B2 (fr)
EP (2) EP3391941B1 (fr)
JP (4) JP7082861B6 (fr)
KR (1) KR102322543B1 (fr)
CN (1) CN106458957B (fr)
AU (2) AU2015243346C9 (fr)
CA (1) CA2944565C (fr)
CY (1) CY1120650T1 (fr)
DK (1) DK3129016T3 (fr)
EA (1) EA035678B1 (fr)
ES (2) ES2953522T3 (fr)
HR (1) HRP20181126T1 (fr)
IL (1) IL247904B (fr)
LT (2) LT3129016T (fr)
MA (2) MA44092B1 (fr)
MX (1) MX378072B (fr)
PL (1) PL3129016T3 (fr)
PT (2) PT3129016T (fr)
RS (1) RS57624B1 (fr)
SG (1) SG11201607907PA (fr)
SI (1) SI3129016T1 (fr)
SM (1) SMT201800429T1 (fr)
TR (1) TR201810411T4 (fr)
WO (1) WO2015155231A1 (fr)
ZA (1) ZA201606608B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106255509A (zh) 2014-04-08 2016-12-21 纽维制药有限公司 用于在归因于线粒体氧化磷酸化的复合体i相关损伤的乳酸性酸中毒或药物诱导的副作用的治疗中应用的琥珀酸酯前药
ES2953522T3 (es) * 2014-04-08 2023-11-14 Abliva Ab Compuestos de succinato novedosos con permeabilidad celular
KR20160143731A (ko) * 2014-04-08 2016-12-14 뉴로바이브 파마슈티컬 에이비 Atp 생산을 증가시키기 위한 숙신산 프로드러그
WO2017060422A1 (fr) * 2015-10-07 2017-04-13 Neurovive Pharmaceutical Ab Métabolites protégés à base d'acide carboxylique pour le traitement des troubles mitochondriaux
WO2017060400A1 (fr) * 2015-10-07 2017-04-13 Neurovive Pharmaceutical Ab Métabolites protégés à base d'acide carboxylique pour le traitement des maladies liées à des dysfonctions mitochondriales
WO2017060418A1 (fr) * 2015-10-07 2017-04-13 Neurovive Pharmaceutical Ab Métabolites protégés à base d'acide carboxylique pour le traitement des maladies liées aux mitochondries
WO2017096270A1 (fr) 2015-12-03 2017-06-08 The Regents Of The University Of California Méthodes de traitement de maladies mitochondriales
EP3863596A4 (fr) * 2018-10-11 2022-08-10 Imbria Pharmaceuticals, Inc. Compositions et procédés de traitement et de prévention de la neuropathie optique héréditaire de leber
JP2022504584A (ja) * 2018-10-11 2022-01-13 インブリア ファーマシューティカルズ， インコーポレイテッド Ｔｃａ回路中間体およびその使用方法
CN109675037B (zh) * 2019-01-25 2021-09-14 南方医科大学 Atp及其受体在制备治疗自闭症药物中的应用
IL288990B2 (en) * 2019-06-19 2025-09-01 Abliva Ab Succinate drug meters, preparations containing the succinate drug meters and its uses

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ES2661009T3 (es) 2012-10-05 2018-03-27 Neurovive Pharmaceutical Ab Succinatos protegidos para mejorar la producción de ATP mitocondrial
CN106255509A (zh) 2014-04-08 2016-12-21 纽维制药有限公司 用于在归因于线粒体氧化磷酸化的复合体i相关损伤的乳酸性酸中毒或药物诱导的副作用的治疗中应用的琥珀酸酯前药
ES2953522T3 (es) * 2014-04-08 2023-11-14 Abliva Ab Compuestos de succinato novedosos con permeabilidad celular
KR20160143731A (ko) 2014-04-08 2016-12-14 뉴로바이브 파마슈티컬 에이비 Atp 생산을 증가시키기 위한 숙신산 프로드러그

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Publication number Publication date
JP7229189B2 (ja) 2023-02-27
EP3391941A1 (fr) 2018-10-24
EP3391941B1 (fr) 2023-06-07
EA201692017A1 (ru) 2017-02-28
KR20160142861A (ko) 2016-12-13
KR102322543B1 (ko) 2021-11-04
JP7082861B2 (ja) 2022-06-09
SI3129016T1 (sl) 2018-10-30
IL247904A0 (en) 2016-11-30
TR201810411T4 (tr) 2018-08-27
JP2021169519A (ja) 2021-10-28
JP2021169518A (ja) 2021-10-28
IL247904B (en) 2020-08-31
CY1120650T1 (el) 2019-12-11
CA2944565C (fr) 2022-11-29
AU2015243346C1 (en) 2019-02-07
LT3391941T (lt) 2023-11-10
SMT201800429T1 (it) 2018-09-13
MX378072B (es) 2025-03-10
US20170105961A1 (en) 2017-04-20
CN106458957B (zh) 2020-08-18
CN106458957A (zh) 2017-02-22
JP2017513829A (ja) 2017-06-01
MX2016012691A (es) 2016-12-16
US11147789B2 (en) 2021-10-19
AU2018282308B2 (en) 2020-04-30
PL3129016T3 (pl) 2018-10-31
US12310940B2 (en) 2025-05-27
BR112016023086A8 (pt) 2021-06-29
EA035678B1 (ru) 2020-07-24
LT3129016T (lt) 2018-09-10
AU2015243346C9 (en) 2019-03-07
PT3391941T (pt) 2023-08-24
AU2015243346B2 (en) 2018-10-18
JP2020100628A (ja) 2020-07-02
BR112016023086A2 (pt) 2017-08-15
EP3129016B1 (fr) 2018-06-06
ZA201606608B (en) 2022-10-26
EP3129016A1 (fr) 2017-02-15
AU2015243346A1 (en) 2016-10-13
US20210401792A1 (en) 2021-12-30
MA44092B1 (fr) 2023-08-31
MA39855A (fr) 2018-10-24
PT3129016T (pt) 2018-10-01
AU2018282308A1 (en) 2019-01-17
HRP20181126T1 (hr) 2018-10-05
ES2683860T3 (es) 2018-09-28
RS57624B1 (sr) 2018-11-30
WO2015155231A1 (fr) 2015-10-15
CA2944565A1 (fr) 2015-10-15
ES2953522T3 (es) 2023-11-14
SG11201607907PA (en) 2016-10-28
DK3129016T3 (en) 2018-09-03
HK1255109A1 (en) 2019-08-02
JP7082861B6 (ja) 2023-12-22

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