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AR083595A1 - Derivados de indol y el proceso para su preparacion - Google Patents

Derivados de indol y el proceso para su preparacion

Info

Publication number
AR083595A1
AR083595A1 ARP110103997A ARP110103997A AR083595A1 AR 083595 A1 AR083595 A1 AR 083595A1 AR P110103997 A ARP110103997 A AR P110103997A AR P110103997 A ARP110103997 A AR P110103997A AR 083595 A1 AR083595 A1 AR 083595A1
Authority
AR
Argentina
Prior art keywords
hydrogen
alkyl
nhr
cycloalkyl
alkenyl
Prior art date
Application number
ARP110103997A
Other languages
English (en)
Original Assignee
Merz Pharma Gmbh & Co Kgaa
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 Merz Pharma Gmbh & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa
Publication of AR083595A1 publication Critical patent/AR083595A1/es

Links

Classifications

    • 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
    • A61K31/40Heterocyclic 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
    • A61K31/403Heterocyclic 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
    • A61K31/404Indoles, e.g. pindolol
    • A61K31/4045Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61K31/40Heterocyclic 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
    • A61K31/403Heterocyclic 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
    • A61K31/404Indoles, e.g. pindolol
    • A61K31/405Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • 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
    • A61P25/22Anxiolytics
    • 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
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32Alcohol-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34Tobacco-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36Opioid-abuse
    • 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
    • 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
    • A61P27/00Drugs for disorders of the senses
    • A61P27/16Otologicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • 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
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Obesity (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Anesthesiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Los compuestos son inhibidores potentes de la polimerización del péptido Ab y se pueden utilizar para el tratamiento de por ejemplo la enfermedad de Alzheimer o trastornos oculares.Reivindicación 1: Un compuesto de la fórmula (1) en donde R1 es hidrógeno, alquilo C1-6, cicloalquilo C3-12, -C(O)-R o -C(O)OR; R2 es hidrógeno, alquilo C1-6 o cicloalquilo C3-12; R3 es-OR, -NHR o -NR2; R4 es hidrógeno, halógeno, ciano, trifluorometilo, alquilo C1-6, arilo C6-10, heteroarilo, -OR, -NHR, -NRR, -C(O)-R o -C(O)-NHR; R5 es hidrógeno, alquilo C1-6 o alquenilo C2-6; R6 es hidrógeno, alquilo C1-6 o alquenilo C2-6; o R5 y R6 conjuntamente con los átomos de carbono que los portan forman un sistema cíclico con 3 a 6 átomos de carbono; R es hidrógeno, alquilo C1-6, o arilo C6-10; X es un grupo -C(O)CH2-, -CH(OH)CH2-, -CH=CH- o -CH2-NH-C(O)-; R7 es hidrógeno, metilo, etilo, propilo o ciclopropilo; o un isómero óptico, sal farmacéuticamente aceptable, hidrato, solvato, o polimorfo de los mismos.
ARP110103997A 2010-10-29 2011-10-28 Derivados de indol y el proceso para su preparacion AR083595A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US40792410P 2010-10-29 2010-10-29
EP10189377 2010-10-29

Publications (1)

Publication Number Publication Date
AR083595A1 true AR083595A1 (es) 2013-03-06

Family

ID=43768707

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP110103997A AR083595A1 (es) 2010-10-29 2011-10-28 Derivados de indol y el proceso para su preparacion

Country Status (13)

Country Link
US (2) US9309196B2 (es)
EP (1) EP2632897B1 (es)
JP (1) JP5848768B2 (es)
KR (1) KR20130132829A (es)
CN (1) CN103282349A (es)
AR (1) AR083595A1 (es)
AU (1) AU2011322565A1 (es)
BR (1) BR112013010549A2 (es)
CA (1) CA2814905A1 (es)
IL (1) IL225771A0 (es)
MX (1) MX2013004760A (es)
RU (1) RU2013124827A (es)
WO (1) WO2012055945A1 (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2044951A1 (en) 2007-10-02 2009-04-08 Merz Pharma GmbH & Co. KGaA The use of substances for the treatment of loss of eyesight in humans with glaucoma and other degenerative eye diseases
BR112013010549A2 (pt) 2010-10-29 2017-10-24 Merz Pharma Gmbh & Co Kgaa derivados indol e processo para sua preparação
TW201412325A (zh) * 2012-06-20 2014-04-01 梅茲製藥有限兩合公司 用於治療患有青光眼及其他退化性眼疾之人類視力喪失的間隔醫療
WO2017218697A1 (en) * 2016-06-17 2017-12-21 The Trustees Columbia University In The City Of New York Identification of compounds that target the rna-binding protein tia-1 an important regulator of stress vulnerability in both mice and humans
JP7402857B2 (ja) * 2018-04-04 2023-12-21 エピオダイン,インク. オピオイド受容体モジュレーター、およびそれに関連する生成物ならびに方法
WO2020219634A1 (en) 2019-04-24 2020-10-29 Galimedix Therapeutics Inc. Indole compounds for use in neurorestoration
EP4000623A1 (en) 2020-11-11 2022-05-25 Consejo Superior De Investigaciones Científicas 5-(2-(1h-indol-3-yl))-ethyl)- piperazin-2-one derivatives for use in the treatment of viral infections by viruses of the family coronaviridae
TW202344248A (zh) * 2022-05-04 2023-11-16 美商加利美德斯治療公司 用於改善解毒效應之相對供應不足的β澱粉樣蛋白聚集抑制劑

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES413944A1 (es) 1972-04-20 1976-06-01 Merz & Co Procedimiento para la preparacion de compuestos de adamen- tano trisustituidos en las posiciones 1,3,5.
DE2856393C2 (de) 1978-12-27 1983-04-28 Merz + Co GmbH & Co, 6000 Frankfurt Arzneimittel zur Behandlung von Morbus Parkinson
US4743585A (en) * 1986-11-21 1988-05-10 Warner-Lambert Company Renin inhibitors
EP0392059B1 (de) 1989-04-14 1993-09-15 Merz & Co. GmbH & Co. Verwendung von Adamantan-Derivaten zur Prävention und Behandlung der cerebralen Ischämie
US7384910B2 (en) * 1997-10-08 2008-06-10 Castillo Gerardo M Small peptides for the treatment of Alzheimer's disease and other beta-amyloid protein fibrillogenesis disorders
JP2006506942A (ja) 2002-01-31 2006-03-02 テル アヴィヴ ユニヴァーシティ フューチャー テクノロジー ディヴェロップメント エル.ピー. アミロイド関連疾患を診断および処置するためのペプチド、それに対する抗体、ならびにその使用方法
US20040072806A1 (en) 2002-03-15 2004-04-15 Zhi-Xing Yao Neuroprotective spirostenol pharmaceutical compositions
CA2530927A1 (en) * 2003-06-30 2005-01-06 Tel Aviv University Future Technology Development L.P. Peptides antibodies directed thereagainst and methods using same for diagnosing and treating amyloid-associated diseases
EP1698189B1 (en) 2003-12-19 2009-05-06 Telefonaktiebolaget LM Ericsson (publ) Relay station and method for enabling reliable digital communications between two nodes in a wireless relay based network
EP2044951A1 (en) 2007-10-02 2009-04-08 Merz Pharma GmbH & Co. KGaA The use of substances for the treatment of loss of eyesight in humans with glaucoma and other degenerative eye diseases
BR112013010549A2 (pt) 2010-10-29 2017-10-24 Merz Pharma Gmbh & Co Kgaa derivados indol e processo para sua preparação

Also Published As

Publication number Publication date
MX2013004760A (es) 2013-07-02
US9309196B2 (en) 2016-04-12
JP2013540796A (ja) 2013-11-07
US20160220535A1 (en) 2016-08-04
JP5848768B2 (ja) 2016-01-27
RU2013124827A (ru) 2014-12-10
IL225771A0 (en) 2013-06-27
US9629824B2 (en) 2017-04-25
WO2012055945A1 (en) 2012-05-03
AU2011322565A1 (en) 2013-05-30
US20130289090A1 (en) 2013-10-31
EP2632897A1 (en) 2013-09-04
EP2632897B1 (en) 2014-10-01
CN103282349A (zh) 2013-09-04
KR20130132829A (ko) 2013-12-05
BR112013010549A2 (pt) 2017-10-24
CA2814905A1 (en) 2012-05-03

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