CA2699289C - Thiazolidinedione analogues for the treatment of hypertension - Google Patents

Thiazolidinedione analogues for the treatment of hypertension Download PDF

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Publication number
CA2699289C
CA2699289C CA2699289A CA2699289A CA2699289C CA 2699289 C CA2699289 C CA 2699289C CA 2699289 A CA2699289 A CA 2699289A CA 2699289 A CA2699289 A CA 2699289A CA 2699289 C CA2699289 C CA 2699289C
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Prior art keywords
aliphatic
mmol
evaporated
vacuo
compounds
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Active
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CA2699289A
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English (en)
French (fr)
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CA2699289A1 (en
Inventor
Gerard R. Colca
Robert C. Gadwood
Tim Parker
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Cirius Therapeutics Inc
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Metabolic Solutions Development Co LLC
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Publication of CA2699289A1 publication Critical patent/CA2699289A1/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34Oxygen atoms
    • 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
    • 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
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • 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
    • A61P25/28Drugs 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
    • 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
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • 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
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pulmonology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Transplantation (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2699289A 2007-09-14 2008-09-15 Thiazolidinedione analogues for the treatment of hypertension Active CA2699289C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US97263907P 2007-09-14 2007-09-14
US60/972,639 2007-09-14
PCT/US2008/010723 WO2009038681A1 (en) 2007-09-14 2008-09-15 Thiazolidinedione analogues for the treatment of hypertension

Publications (2)

Publication Number Publication Date
CA2699289A1 CA2699289A1 (en) 2009-03-26
CA2699289C true CA2699289C (en) 2016-01-19

Family

ID=40239575

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2699289A Active CA2699289C (en) 2007-09-14 2008-09-15 Thiazolidinedione analogues for the treatment of hypertension

Country Status (15)

Country Link
US (1) US8067450B2 (enExample)
EP (1) EP2203433B1 (enExample)
JP (1) JP5371988B2 (enExample)
KR (1) KR101537830B1 (enExample)
CN (1) CN101848901B (enExample)
AU (1) AU2008301905B2 (enExample)
BR (1) BRPI0817096B8 (enExample)
CA (1) CA2699289C (enExample)
ES (1) ES2398313T3 (enExample)
IL (1) IL204440A (enExample)
MX (1) MX2010002820A (enExample)
NZ (2) NZ597381A (enExample)
PL (1) PL2203433T3 (enExample)
RU (1) RU2486179C2 (enExample)
WO (1) WO2009038681A1 (enExample)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5269758B2 (ja) 2006-03-16 2013-08-21 メタボリック ソリューションズ ディベロップメント カンパニー, エルエルシー 代謝性炎症によって媒介される疾患を処置するためのチアゾリジンジオン類似体
CN101454006B (zh) 2006-03-16 2012-12-26 新陈代谢解决方案开发公司 用于治疗高血压以及用于降低血脂的噻唑烷二酮类似物
US8304441B2 (en) 2007-09-14 2012-11-06 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues for the treatment of metabolic diseases
BRPI0817096B8 (pt) 2007-09-14 2021-05-25 Cirius Therapeutics Inc análogo de tiazolidinodiona e composição farmacêutica que o compreende
US8722710B2 (en) 2007-09-26 2014-05-13 Deuterx, Llc Deuterium-enriched pioglitazone
WO2010105048A1 (en) * 2009-03-12 2010-09-16 Metabolic Solutions Development Company Thiazolidinedione analogues
EP2512475A1 (en) * 2009-12-15 2012-10-24 Metabolic Solutions Development Company LLC Ppar-sparing thiazolidinediones and combinations for the treatment of obesity and other metabolic diseases
AU2014202074B2 (en) * 2009-12-15 2016-01-07 Cirius Therapeutics, Inc. PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases
NO2513070T3 (enExample) 2009-12-15 2018-04-07
PL2512470T3 (pl) * 2009-12-15 2017-06-30 Octeta Therapeutics, Llc Oszczędzające ppar tiazolidynodiony i połączenia do leczenia chorób neurodegeneracyjnych
JP2013514369A (ja) * 2009-12-15 2013-04-25 メタボリック ソリューションズ ディベロップメント カンパニー, エルエルシー 糖尿病および他の代謝性疾患を処置するための、ppar温存チアゾリジンジオンおよび組み合わせ物
WO2011107494A1 (de) 2010-03-03 2011-09-09 Sanofi Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
US8937182B2 (en) 2010-04-19 2015-01-20 Metabolic Solutions Development Company, Llc Synthesis for thiazolidinedione compounds
US20130281414A1 (en) * 2010-04-21 2013-10-24 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues
US8530413B2 (en) 2010-06-21 2013-09-10 Sanofi Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
EP2603498B1 (en) * 2010-08-10 2016-11-09 Octeta Therapeutics, LLC Novel synthesis for thiazolidinedione compounds
CA2807815C (en) 2010-08-10 2018-10-02 Metabolic Solutions Development Company, Llc Novel synthesis for thiazolidinedione compounds
WO2012109495A1 (en) * 2011-02-09 2012-08-16 Metabolic Solutions Development Company, Llc Cellular targets of thiazolidinediones
WO2012149083A1 (en) * 2011-04-28 2012-11-01 Metabolic Solutions Development Company, Llc Ppar-sparing thiazolidinediones for the treatment of kidney related diseases
WO2013037390A1 (en) 2011-09-12 2013-03-21 Sanofi 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
EP2760862B1 (en) 2011-09-27 2015-10-21 Sanofi 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013068486A1 (en) 2011-11-08 2013-05-16 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for the diagnosis and treatment of male infertility
EP2968298B1 (en) 2013-03-14 2018-01-31 Deuterx, LLC Deuterium-enriched 2,4-thiazolidinediones and methods of treatment
RU2687490C2 (ru) 2013-07-22 2019-05-14 МЕТАБОЛИК СОЛЮШИНС ДЕВЕЛОПМЕНТ КО., ЭлЭлСи Ppar-поддерживающие соединения для лечения метаболических заболеваний
EP3094328B1 (en) 2014-01-15 2020-08-19 Poxel SA Methods of treating neurological, metabolic, and other disorders using enantiopure deuterium-enriched pioglitazone
US20210038566A1 (en) 2018-02-08 2021-02-11 Enyo Pharma Use of modulators of neet proteins for the treatment of infection
US11319313B2 (en) 2020-06-30 2022-05-03 Poxel Sa Crystalline forms of deuterium-enriched pioglitazone
US11767317B1 (en) 2020-06-30 2023-09-26 Poxel Sa Methods of synthesizing enantiopure deuterium-enriched pioglitazone
GB202210503D0 (en) 2022-07-18 2022-08-31 Univ Court Univ Of Glasgow Materials and methods for treatment of chronic myeloid leukemia (CML)

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5522636A (en) * 1978-08-04 1980-02-18 Takeda Chem Ind Ltd Thiazoliding derivative
US4582839A (en) 1984-03-21 1986-04-15 Takeda Chemical Industries, Ltd. 2,4-thiazolidinediones
CN1003445B (zh) 1984-10-03 1989-03-01 武田药品工业株式会社 噻唑烷二酮衍生物,其制备方法和用途
WO1986002073A1 (fr) 1984-10-03 1986-04-10 Takeda Chemical Industries, Ltd. Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant
AR240698A1 (es) 1985-01-19 1990-09-28 Takeda Chemical Industries Ltd Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales
US5167228A (en) 1987-06-26 1992-12-01 Brigham And Women's Hospital Assessment and modification of endogenous circadian phase and amplitude
US5356913A (en) 1990-02-09 1994-10-18 The Upjohn Company Use of insulin sensitizing agents to treat hypertension
KR100249988B1 (ko) 1991-04-11 2000-04-01 로렌스 티. 마이젠헬더 티아졸리딘디온 유도체, 그의 제조방법 및 용도
US5441971A (en) 1991-04-11 1995-08-15 The Upjohn Company Thiazolidinedione derivatives, production and use thereof
NO302471B1 (no) * 1991-12-26 1998-03-09 Sankyo Co Tiazolidinforbindelser og farmasöytisk preparat
US5994341A (en) 1993-07-19 1999-11-30 Angiogenesis Technologies, Inc. Anti-angiogenic Compositions and methods for the treatment of arthritis
IL113313A (en) * 1994-04-11 1999-09-22 Sankyo Co Heterocyclic compounds and pharmaceutical compositions containing the same
US6099562A (en) 1996-06-13 2000-08-08 Schneider (Usa) Inc. Drug coating with topcoat
TW438587B (en) * 1995-06-20 2001-06-07 Takeda Chemical Industries Ltd A pharmaceutical composition for prophylaxis and treatment of diabetes
CA2180296C (en) 1995-07-03 2007-01-09 Yoshio Tsujita Treatment of arteriosclerosis and xanthoma
JP2002543118A (ja) 1999-04-29 2002-12-17 シティ・オブ・ホープ ペントキシフィリン、ピオグリタゾンおよびメトフォルミンは、後期糖化最終生成物(age)の形成の阻害剤である
DK1192137T3 (da) 1999-06-30 2013-11-11 Amgen Inc Forbindelser til modulering af PPAR-gamma aktivitet
AU6118001A (en) 2000-05-03 2001-11-12 Tularik Inc Combination therapeutic compositions and methods of use
SK14452003A3 (sk) 2001-04-26 2004-04-06 Liva, A. S. Spôsob výroby pioglitazonu ako antidiabetika
WO2003026586A2 (en) 2001-09-28 2003-04-03 Teva Pharmaceutical Industries Ltd. Pioglitazone hydrochloride
DE60316152D1 (de) 2002-07-16 2007-10-18 Cadila Healthcare Ltd Prozess zur herstellung von pioglitazon via verschiedene zwischenstufen
WO2004082715A1 (ja) * 2003-03-20 2004-09-30 Eisai Co., Ltd. 炎症性腸疾患治療剤としての併用医薬
US7230016B2 (en) 2003-05-13 2007-06-12 Synthon Ip Inc. Pioglitazone salts, such as pioglitazone sulfate, and pharmaceutical compositions and processes using the same
JP2005015477A (ja) * 2003-06-06 2005-01-20 Takeda Chem Ind Ltd 固形製剤
US20070078170A1 (en) 2003-08-28 2007-04-05 Khanduri Chandra H Process for the preparation of pioglitazone
AR047541A1 (es) 2004-02-13 2006-01-25 Sandoz Ag Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas
ES2393197T3 (es) 2004-09-28 2012-12-19 Otsuka Pharmaceutical Co., Ltd. Compuesto de carbostirilo
JP5269758B2 (ja) 2006-03-16 2013-08-21 メタボリック ソリューションズ ディベロップメント カンパニー, エルエルシー 代謝性炎症によって媒介される疾患を処置するためのチアゾリジンジオン類似体
CN101454006B (zh) * 2006-03-16 2012-12-26 新陈代谢解决方案开发公司 用于治疗高血压以及用于降低血脂的噻唑烷二酮类似物
AU2007227552A1 (en) 2006-03-16 2007-09-27 Metabolic Solutions Development Company Combination therapies of thiazolidinedione analogues and glucocorticoid agonists
BRPI0817096B8 (pt) 2007-09-14 2021-05-25 Cirius Therapeutics Inc análogo de tiazolidinodiona e composição farmacêutica que o compreende
WO2010105048A1 (en) 2009-03-12 2010-09-16 Metabolic Solutions Development Company Thiazolidinedione analogues

Also Published As

Publication number Publication date
WO2009038681A1 (en) 2009-03-26
BRPI0817096B1 (pt) 2020-11-10
JP2010539171A (ja) 2010-12-16
KR20100075915A (ko) 2010-07-05
RU2486179C2 (ru) 2013-06-27
IL204440A (en) 2013-05-30
KR101537830B1 (ko) 2015-07-17
BRPI0817096B8 (pt) 2021-05-25
MX2010002820A (es) 2010-04-01
EP2203433B1 (en) 2012-10-31
HK1146484A1 (en) 2011-06-10
BRPI0817096A2 (pt) 2017-05-02
BRPI0817096A8 (pt) 2017-10-10
CA2699289A1 (en) 2009-03-26
NZ597381A (en) 2013-03-28
CN101848901B (zh) 2012-11-21
US20100222399A1 (en) 2010-09-02
JP5371988B2 (ja) 2013-12-18
NZ583889A (en) 2012-01-12
CN101848901A (zh) 2010-09-29
ES2398313T3 (es) 2013-03-15
AU2008301905A1 (en) 2009-03-26
PL2203433T3 (pl) 2013-04-30
EP2203433A1 (en) 2010-07-07
US8067450B2 (en) 2011-11-29
RU2010114727A (ru) 2011-10-20
AU2008301905B2 (en) 2013-06-27

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