CA2306692C - Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers - Google Patents

Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers Download PDF

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Publication number
CA2306692C
CA2306692C CA2306692A CA2306692A CA2306692C CA 2306692 C CA2306692 C CA 2306692C CA 2306692 A CA2306692 A CA 2306692A CA 2306692 A CA2306692 A CA 2306692A CA 2306692 C CA2306692 C CA 2306692C
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Prior art keywords
asp
ch2f
compound
cbz
pharmaceutically acceptable
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Expired - Fee Related
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CA2306692A
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CA2306692A1 (fr
Inventor
John F. W. Keana
Sui Xiong Cai
John Guastella
Wu Yang
John A. Drewe
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Cytovia Therapeutics LLC
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Cytovia Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/10—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2810/00—Vectors comprising a targeting moiety
    • C12N2810/40—Vectors comprising a peptide as targeting moiety, e.g. a synthetic peptide, from undefined source

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Psychology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Transplantation (AREA)
  • Genetics & Genomics (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Biochemistry (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Endocrinology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Orthopedic Medicine & Surgery (AREA)

Abstract

La présente invention concerne de nouveaux dipeptides représentés par la formule générale (I), dans laquelle R1-R3 et AA sont définis. Les composés correspondant à la formule (I) sont de puissants inhibiteurs de la mort cellulaire programmée. Par conséquent, les inhibiteurs décrits dans la présente invention peuvent retarder ou bloquer la mort cellulaire dans diverses conditions cliniques pouvant donner lieu à la perte de cellules, de tissus ou de la totalité des organes.
CA2306692A 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers Expired - Fee Related CA2306692C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6167697P 1997-10-10 1997-10-10
US60/061,676 1997-10-10
PCT/US1998/021232 WO1999018781A1 (fr) 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers

Publications (2)

Publication Number Publication Date
CA2306692A1 CA2306692A1 (fr) 1999-04-22
CA2306692C true CA2306692C (fr) 2010-09-21

Family

ID=22037372

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2306692A Expired - Fee Related CA2306692C (fr) 1997-10-10 1998-10-09 Dipeptides inhibiteurs de l'apoptose et utilisation de ces derniers

Country Status (10)

Country Link
EP (1) EP1033910A4 (fr)
JP (1) JP4439111B2 (fr)
KR (1) KR100580333B1 (fr)
CN (1) CN1138472C (fr)
AU (1) AU741203B2 (fr)
BR (1) BR9814817A (fr)
CA (1) CA2306692C (fr)
EA (1) EA200000409A1 (fr)
NO (1) NO20001323L (fr)
WO (1) WO1999018781A1 (fr)

Families Citing this family (33)

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Publication number Priority date Publication date Assignee Title
US6184210B1 (en) 1997-10-10 2001-02-06 Cytovia, Inc. Dipeptide apoptosis inhibitors and the use thereof
ATE295177T1 (de) * 1998-03-16 2005-05-15 Cytovia Inc Dipeptid kaspase inhibitoren und deren verwendung
WO1999062554A1 (fr) 1998-05-29 1999-12-09 Mochida Pharmaceutical Co., Ltd. Preparations de prevention / de traitement de maladies demyelinisantes auto-immunes
AU773891C (en) 1998-10-23 2005-02-17 Kirin-Amgen Inc. Dimeric thrombopoietin peptide mimetics binding to MP1 receptor and having thrombopoietic activity
US7488590B2 (en) 1998-10-23 2009-02-10 Amgen Inc. Modified peptides as therapeutic agents
US6660843B1 (en) 1998-10-23 2003-12-09 Amgen Inc. Modified peptides as therapeutic agents
WO2000044216A2 (fr) 1999-02-01 2000-08-03 Cytovia Inc Acide de gomme-gute,. analogues et derives en tant qu'activateurs de caspases et inducteurs d'apoptose
EP1165490B1 (fr) 1999-03-16 2006-08-16 Cytovia, Inc. Inhibiteurs de caspases 2-aminobenzamidiques substitues et leur utilisation
ATE363465T1 (de) 1999-04-09 2007-06-15 Cytovia Inc Caspase inhibitoren und ihre verwendung
EA200200301A1 (ru) 1999-08-27 2002-08-29 Сайтовиэ, Инк. ЗАМЕЩЕННЫЕ α-ГИДРОКСИКИСЛОТЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБ ИНГИБИРОВАНИЯ КЛЕТОЧНОЙ ГИБЕЛИ НА КЛЕТОЧНОМ ИЛИ ТКАНЕВОМ УРОВНЕ, СПОСОБ ЛЕЧЕНИЯ ИЛИ ОБЛЕГЧЕНИЯ СОСТОЯНИЯ ПРИ ГИБЕЛИ КЛЕТОК У ЖИВОТНОГО, СПОСОБ ЛЕЧЕНИЯ ИЛИ ПРОФИЛАКТИКИ РАЗЛИЧНЫХ БОЛЕЗНЕЙ
US6566338B1 (en) 1999-10-12 2003-05-20 Cytovia, Inc. Caspase inhibitors for the treatment and prevention of chemotherapy and radiation therapy induced cell death
US6303374B1 (en) 2000-01-18 2001-10-16 Isis Pharmaceuticals Inc. Antisense modulation of caspase 3 expression
DE10006889A1 (de) * 2000-02-16 2001-09-06 Procorde Gmbh Verwendung von Inhibitoren von Caspase-3 oder der Caspase-aktivierten Desoxyribonuclease (CAD) zur Behandlung von Herzerkrankungen
CN1994298A (zh) * 2000-03-29 2007-07-11 沃泰克斯药物股份有限公司 氨基甲酸酯天冬氨酸特异性半胱氨酸蛋白酶抑制剂及其用途
SI1268425T1 (sl) 2000-03-29 2008-04-30 Vertex Pharma Zaviralci karbamat kaspaze in uporaba le-teh
AU2001265008A1 (en) * 2000-05-23 2001-12-03 Vertex Pharmaceuticals Incorporated Caspase inhibitors and uses thereof
US20020052323A1 (en) * 2000-08-30 2002-05-02 Jinhai Wang Quinoline-(C=O)-(multiple amino acids)-leaving group compounds for pharmaceutical compositions and reagents
US6800619B2 (en) 2000-09-13 2004-10-05 Vertex Pharmaceuticals Incorporated Caspase inhibitors and uses thereof
HUP0302173A2 (hu) 2000-09-15 2003-09-29 Vertex Pharmaceuticals Incorporated Protein kináz inhibitorokként alkalmazható pirazolvegyületek
US6660731B2 (en) 2000-09-15 2003-12-09 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
ES2265452T3 (es) 2000-12-21 2007-02-16 Vertex Pharmaceuticals Incorporated Compuestos de pirazol utiles como inhibidores de la proteina quinasa.
MXPA03009647A (es) 2001-04-19 2004-01-29 Vertex Pharma Heterociclildicarbamidas como inhibidores de caspasa.
MY141867A (en) 2002-06-20 2010-07-16 Vertex Pharma Substituted pyrimidines useful as protein kinase inhibitors
WO2004013140A1 (fr) 2002-08-02 2004-02-12 Vertex Pharmaceuticals Incorporated Compositions pyrazole convenant comme inhibiteurs de gsk-3
CA2501196A1 (fr) * 2002-10-10 2004-04-22 Becton, Dickinson And Company Systeme collecteur d'echantillons avec inhibiteur de caspase
US8008453B2 (en) 2005-08-12 2011-08-30 Amgen Inc. Modified Fc molecules
AR056763A1 (es) 2005-11-03 2007-10-24 Vertex Pharma Aminopirimidinas sustituidas con tiazol o pirazol,utiles como agentes anticancer y composiciones farmaceuticas que las contienen.
CA2685876A1 (fr) 2007-05-02 2008-11-13 Vertex Pharmaceuticals Incorporated Thiazoles et pyrazoles qui s'utilisent comme inhibiteurs de kinase
WO2009018415A1 (fr) 2007-07-31 2009-02-05 Vertex Pharmaceuticals Incorporated Procédé de préparation de la 5-fluoro-1h-pyrazolo[3,4-b]pyridin-3-amine et des dérivés de celle-ci
FR2923160B1 (fr) * 2007-11-02 2013-07-26 Pasteur Institut Composes destines a prevenir ou traiter une infection virale.
EP2323622A1 (fr) 2008-09-03 2011-05-25 Vertex Pharmaceuticals Incorporated Co-cristaux et formulations pharmaceutiques les comprenant
CN106317161B (zh) * 2015-06-29 2020-05-15 深圳翰宇药业股份有限公司 一种氟甲基酮肽系列化合物的制备方法
CN117045634A (zh) * 2022-05-06 2023-11-14 北京康蒂尼药业股份有限公司 一种二肽衍生物组合物及其制备方法和用途

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Also Published As

Publication number Publication date
AU741203B2 (en) 2001-11-22
EP1033910A4 (fr) 2004-11-24
KR100580333B1 (ko) 2006-05-16
CA2306692A1 (fr) 1999-04-22
NO20001323D0 (no) 2000-03-14
JP2001519358A (ja) 2001-10-23
AU9793098A (en) 1999-05-03
CN1301131A (zh) 2001-06-27
EP1033910A1 (fr) 2000-09-13
EA200000409A1 (ru) 2000-10-30
KR20010031053A (ko) 2001-04-16
NO20001323L (no) 2000-06-13
CN1138472C (zh) 2004-02-18
WO1999018781A1 (fr) 1999-04-22
BR9814817A (pt) 2002-01-08
JP4439111B2 (ja) 2010-03-24

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