BR112014032338A2 - cristais de sal - Google Patents

cristais de sal

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Publication number
BR112014032338A2
BR112014032338A2 BR112014032338-0A BR112014032338A BR112014032338A2 BR 112014032338 A2 BR112014032338 A2 BR 112014032338A2 BR 112014032338 A BR112014032338 A BR 112014032338A BR 112014032338 A2 BR112014032338 A2 BR 112014032338A2
Authority
BR
Brazil
Prior art keywords
salt
salt crystals
crystals
methyl
cyclopent
Prior art date
Application number
BR112014032338-0A
Other languages
English (en)
Other versions
BR112014032338B1 (pt
Inventor
Li Peng
P. Wennogle Lawrence
Davis Robert
Buckton Graham
Hooper Mark
Original Assignee
Intra-Cellular Therapies, Inc.
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
Application filed by Intra-Cellular Therapies, Inc. filed Critical Intra-Cellular Therapies, Inc.
Publication of BR112014032338A2 publication Critical patent/BR112014032338A2/pt
Publication of BR112014032338B1 publication Critical patent/BR112014032338B1/pt

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12Heterocyclic 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 three hetero rings
    • C07D487/14Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • A61P27/06Antiglaucoma agents or miotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02Dicarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13Dicarboxylic acids
    • C07C57/15Fumaric acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Reproductive Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Gynecology & Obstetrics (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

resumo “cristais de sal” a presente invenção se refere um sal de adição ácida e a cristais de sal de (6ar,9as)-5,6a,7,8,9,9a-hexahidro-5-metil-3-(fenilamino)-2-((4-(6-fluoropiridin-2-il)fenil)metil)-ciclopent[4,5]imidazo[1,2-a]pirazolo[4,3-e]pirimidin-4(2h)-ona, a uma composição que compreende o mesmo e o método de produzir e usar o referido sal e os cristais.
BR112014032338-0A 2012-06-21 2013-06-21 Formas cristalinas de (6ar,9as)-5,6a,7,8,9,9a-hexahidro-5-metil-3-(fenilamino)-2-((4-(6- fluoropiridin-2-il)fenil)metil)-ciclopent[4,5] imidazo [1,2-a]pirazol[4,3-e]pirimidin-4(2h)-ona BR112014032338B1 (pt)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261662355P 2012-06-21 2012-06-21
US61/662,355 2012-06-21
US61/662.355 2012-06-21
PCT/US2013/047123 WO2013192556A2 (en) 2012-06-21 2013-06-21 Salt crystals

Publications (2)

Publication Number Publication Date
BR112014032338A2 true BR112014032338A2 (pt) 2018-05-15
BR112014032338B1 BR112014032338B1 (pt) 2022-04-26

Family

ID=49769726

Family Applications (2)

Application Number Title Priority Date Filing Date
BR112014032338-0A BR112014032338B1 (pt) 2012-06-21 2013-06-21 Formas cristalinas de (6ar,9as)-5,6a,7,8,9,9a-hexahidro-5-metil-3-(fenilamino)-2-((4-(6- fluoropiridin-2-il)fenil)metil)-ciclopent[4,5] imidazo [1,2-a]pirazol[4,3-e]pirimidin-4(2h)-ona
BR122021026665-4A BR122021026665B1 (pt) 2012-06-21 2013-06-21 Formas cristalinas de (6ar,9as)-5,6a,7,8,9,9a-hexahidro-5-metil-3-(fenilamino)-2-((4-(6- fluoropiridin-2-il)fenil)metil)-ciclopent [4,5] imidazo [1,2-a]pirazol[4,3-e]pirimidin-4(2h)-ona

Family Applications After (1)

Application Number Title Priority Date Filing Date
BR122021026665-4A BR122021026665B1 (pt) 2012-06-21 2013-06-21 Formas cristalinas de (6ar,9as)-5,6a,7,8,9,9a-hexahidro-5-metil-3-(fenilamino)-2-((4-(6- fluoropiridin-2-il)fenil)metil)-ciclopent [4,5] imidazo [1,2-a]pirazol[4,3-e]pirimidin-4(2h)-ona

Country Status (19)

Country Link
US (1) US9469647B2 (pt)
EP (2) EP3733675A1 (pt)
JP (3) JP6506687B2 (pt)
KR (1) KR102175024B1 (pt)
CN (2) CN104602695B (pt)
AR (2) AR091507A1 (pt)
AU (1) AU2013278081B2 (pt)
BR (2) BR112014032338B1 (pt)
CA (1) CA2876001C (pt)
DK (1) DK2863918T3 (pt)
ES (1) ES2769523T3 (pt)
HK (1) HK1210017A1 (pt)
IL (2) IL236069B (pt)
MX (1) MX352831B (pt)
PL (1) PL2863918T3 (pt)
RU (1) RU2652116C2 (pt)
TW (1) TWI652271B (pt)
UY (1) UY34870A (pt)
WO (1) WO2013192556A2 (pt)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8273750B2 (en) 2005-06-06 2012-09-25 Takeda Pharmaceutical Company Limited Organic compounds
EP2089034A4 (en) 2006-12-05 2010-07-28 Intra Cellular Therapies Inc NEW USES
WO2009075784A1 (en) 2007-12-06 2009-06-18 Intra-Cellular Therapies, Inc. Organic compounds
JP2012518685A (ja) 2009-02-25 2012-08-16 イントラ−セルラー・セラピーズ・インコーポレイテッド 眼障害のためのpde1阻害剤
EP2434895A4 (en) 2009-05-13 2013-08-07 Intra Cellular Therapies Inc ORGANIC CONNECTIONS
TW201206937A (en) 2010-05-31 2012-02-16 Intra Cellular Therapies Inc Organic compounds
US9763948B2 (en) 2010-05-31 2017-09-19 Intra-Cellular Therapies, Inc. PDE1 inhibitory compounds and methods
AR091507A1 (es) * 2012-06-21 2015-02-11 Intra Cellular Therapies Inc SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA
JP6549040B2 (ja) 2013-02-17 2019-07-24 イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. 新規使用
EP2968338B1 (en) * 2013-03-15 2019-01-09 Intra-Cellular Therapies, Inc. Pde1 inhibitors for use in the treatment and/or prevention of cns injuries, and pns diseases, disorders or injuries
CN105377846B (zh) 2013-03-15 2018-03-20 细胞内治疗公司 有机化合物
CN110498800A (zh) * 2013-06-21 2019-11-26 细胞内治疗公司 游离碱晶体
EP3091983B1 (en) * 2014-01-08 2019-10-02 Intra-Cellular Therapies, Inc. Pharmaceutical compositions comprising a pde-1 inhibitor and a pde-2 inhibitor
JP6810613B2 (ja) * 2014-06-20 2021-01-06 イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. 有機化合物
US10131671B2 (en) 2014-08-07 2018-11-20 Intra-Cellular Therapies, Inc. Organic compounds
US10285992B2 (en) 2014-08-07 2019-05-14 Intra-Cellular Therapies, Inc. Combinations of PDE1 inhibitors and NEP inhibitors and associated methods
EP3193878B1 (en) 2014-09-17 2021-01-06 Intra-Cellular Therapies, Inc. 7,8-dihydro-[2h]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5h)-one derivatives as phosphodiesterase 1 (pde1) inhibitors for treating diseases, disorders or injuries of the central nervous system (cns)
BR112017012005B1 (pt) 2014-12-06 2023-04-04 Intra-Cellular Therapies, Inc Compostos orgânicos inibidores de pde2, composições farmacêuticas compreendendo os ditos compostos e uso dos mesmos no tratamento de um distúrbio mediado por pde2
BR112017012007B1 (pt) 2014-12-06 2022-11-01 Intra-Cellular Therapies, Inc Compostos orgânicos inibitórios de pde2, composições farmacêuticas compreendendo os ditos compostos e uso dos mesmos no tratamento de um distúrbio mediado por pde2
WO2017172795A1 (en) 2016-03-28 2017-10-05 Intra-Cellular Therapies, Inc. Novel compositions and methods
ES2906107T3 (es) 2016-09-12 2022-04-13 Intra Cellular Therapies Inc Usos novedosos
WO2019152697A1 (en) 2018-01-31 2019-08-08 Intra-Cellular Therapies, Inc. Novel uses
WO2023147603A2 (en) * 2022-01-31 2023-08-03 Intra-Cellular Therapies, Inc. Salt crystals

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TWI265925B (en) 1999-10-11 2006-11-11 Pfizer Pyrazolo[4,3-d]pyrimidin-7-ones useful in inhibiting type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases(cGMP PDE5), process and intermediates for their preparation, their uses and composition comprising them
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US8273750B2 (en) * 2005-06-06 2012-09-25 Takeda Pharmaceutical Company Limited Organic compounds
US9198924B2 (en) 2006-11-13 2015-12-01 Intra-Cellular Therapies, Inc. Organic compounds
EP2089034A4 (en) 2006-12-05 2010-07-28 Intra Cellular Therapies Inc NEW USES
WO2009075784A1 (en) 2007-12-06 2009-06-18 Intra-Cellular Therapies, Inc. Organic compounds
EP2370080A1 (en) 2008-12-02 2011-10-05 University of Utah Research Foundation Pde1 as a target therapeutic in heart disease
CN102232077A (zh) 2008-12-06 2011-11-02 细胞内治疗公司 有机化合物
EA201170769A1 (ru) 2008-12-06 2012-02-28 Интра-Селлулар Терапиз, Инк. Органические соединения
MA32938B1 (fr) 2008-12-06 2012-01-02 Intra Cellular Therapies Inc Composes organiques
JP2012518685A (ja) 2009-02-25 2012-08-16 イントラ−セルラー・セラピーズ・インコーポレイテッド 眼障害のためのpde1阻害剤
EP2434895A4 (en) 2009-05-13 2013-08-07 Intra Cellular Therapies Inc ORGANIC CONNECTIONS
US8858911B2 (en) 2009-10-08 2014-10-14 Intra-Cellular Therapies, Inc. Phosphodiesterase 1-targeting tracers and methods
TW201206937A (en) 2010-05-31 2012-02-16 Intra Cellular Therapies Inc Organic compounds
US9763948B2 (en) 2010-05-31 2017-09-19 Intra-Cellular Therapies, Inc. PDE1 inhibitory compounds and methods
WO2012171016A1 (en) 2011-06-10 2012-12-13 Intra-Cellular Therapies, Inc. Organic compounds
AR091507A1 (es) * 2012-06-21 2015-02-11 Intra Cellular Therapies Inc SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA
CN110498800A (zh) * 2013-06-21 2019-11-26 细胞内治疗公司 游离碱晶体

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JP2015520243A (ja) 2015-07-16
IL236069B (en) 2020-04-30
JP6506687B2 (ja) 2019-04-24
RU2015101647A (ru) 2016-08-10
EP2863918A4 (en) 2016-01-13
CN104602695A (zh) 2015-05-06
JP2018065868A (ja) 2018-04-26
WO2013192556A2 (en) 2013-12-27
UY34870A (es) 2014-01-31
EP2863918A2 (en) 2015-04-29
AU2013278081B2 (en) 2017-06-29
AR120339A2 (es) 2022-02-09
AR091507A1 (es) 2015-02-11
CN104602695B (zh) 2017-08-29
HK1210017A1 (en) 2016-04-15
RU2652116C2 (ru) 2018-04-25
KR20150023386A (ko) 2015-03-05
AU2013278081A1 (en) 2015-01-22
JP2020012003A (ja) 2020-01-23
DK2863918T3 (da) 2020-03-23
MX352831B (es) 2017-12-11
JP6853794B2 (ja) 2021-03-31
EP2863918B1 (en) 2019-12-25
WO2013192556A3 (en) 2014-02-27
IL236069A0 (en) 2015-01-29
CA2876001A1 (en) 2013-12-27
ES2769523T3 (es) 2020-06-26
PL2863918T3 (pl) 2020-05-18
MX2014015904A (es) 2015-07-17
CN107602572A (zh) 2018-01-19
IL273276A (en) 2020-04-30
CA2876001C (en) 2021-06-08
BR122021026665B1 (pt) 2022-12-06
EP3733675A1 (en) 2020-11-04
KR102175024B1 (ko) 2020-11-05
TW201406763A (zh) 2014-02-16
BR112014032338B1 (pt) 2022-04-26
US20150259353A1 (en) 2015-09-17
TWI652271B (zh) 2019-03-01
US9469647B2 (en) 2016-10-18

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