PE20070365A1 - Forma cristalina de n-[2-(7-metoxi-1-naftil)etil]acetamida (agomelatina), su procedimiento de preparacion y las composiciones farmaceuticas que la contienen - Google Patents

Forma cristalina de n-[2-(7-metoxi-1-naftil)etil]acetamida (agomelatina), su procedimiento de preparacion y las composiciones farmaceuticas que la contienen

Info

Publication number
PE20070365A1
PE20070365A1 PE2006000868A PE2006000868A PE20070365A1 PE 20070365 A1 PE20070365 A1 PE 20070365A1 PE 2006000868 A PE2006000868 A PE 2006000868A PE 2006000868 A PE2006000868 A PE 2006000868A PE 20070365 A1 PE20070365 A1 PE 20070365A1
Authority
PE
Peru
Prior art keywords
agomelatin
crystalline form
metoxy
acetamide
naphthyl
Prior art date
Application number
PE2006000868A
Other languages
English (en)
Spanish (es)
Inventor
Gerard Coquerel
Julie Linol
Jean-Claude Souvie
Original Assignee
Servier Lab
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=36581629&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20070365(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Servier Lab filed Critical Servier Lab
Publication of PE20070365A1 publication Critical patent/PE20070365A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18—Feminine contraceptives
    • 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
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Anesthesiology (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pregnancy & Childbirth (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Steroid Compounds (AREA)
PE2006000868A 2005-08-03 2006-07-19 Forma cristalina de n-[2-(7-metoxi-1-naftil)etil]acetamida (agomelatina), su procedimiento de preparacion y las composiciones farmaceuticas que la contienen PE20070365A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0508278A FR2889523B1 (fr) 2005-08-03 2005-08-03 Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent

Publications (1)

Publication Number Publication Date
PE20070365A1 true PE20070365A1 (es) 2007-06-02

Family

ID=36581629

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2006000868A PE20070365A1 (es) 2005-08-03 2006-07-19 Forma cristalina de n-[2-(7-metoxi-1-naftil)etil]acetamida (agomelatina), su procedimiento de preparacion y las composiciones farmaceuticas que la contienen

Country Status (37)

Country Link
EP (2) EP2277857A3 (enExample)
JP (1) JP4575337B2 (enExample)
CN (1) CN100448843C (enExample)
AP (1) AP2486A (enExample)
AR (1) AR057715A1 (enExample)
AU (1) AU2006203342B2 (enExample)
BR (1) BRPI0603059A (enExample)
CA (1) CA2555115C (enExample)
CR (1) CR8529A (enExample)
CU (1) CU20060153A7 (enExample)
CY (1) CY1113011T1 (enExample)
DK (1) DK1752443T3 (enExample)
EA (1) EA011030B1 (enExample)
EC (1) ECSP066715A (enExample)
ES (1) ES2391406T3 (enExample)
FR (1) FR2889523B1 (enExample)
GT (1) GT200600346A (enExample)
HR (1) HRP20120779T1 (enExample)
IL (1) IL177173A (enExample)
JO (1) JO2793B1 (enExample)
MA (1) MA28451B1 (enExample)
ME (1) ME02026B (enExample)
MX (1) MXPA06008789A (enExample)
MY (1) MY139902A (enExample)
NO (1) NO336967B1 (enExample)
NZ (1) NZ548864A (enExample)
PE (1) PE20070365A1 (enExample)
PL (1) PL1752443T3 (enExample)
PT (1) PT1752443E (enExample)
RS (1) RS52423B (enExample)
SA (1) SA06270255B1 (enExample)
SG (1) SG130110A1 (enExample)
SI (1) SI1752443T1 (enExample)
TW (1) TWI359128B (enExample)
UA (1) UA83720C2 (enExample)
WO (1) WO2007015004A2 (enExample)
ZA (1) ZA200606453B (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2934856B1 (fr) 2008-08-05 2010-08-13 Servier Lab Nouveau procede d'obtention de la forme cristalline v de l'agomelatine
CN101481321B (zh) * 2009-02-27 2012-04-18 上海医药工业研究院 阿戈美拉汀卤化氢复合物及其制备方法
CN101585779B (zh) * 2009-03-10 2014-04-02 上海医药工业研究院 阿戈美拉汀的晶型vi及其制备方法和应用
WO2011006387A1 (zh) * 2009-07-11 2011-01-20 浙江华海药业股份有限公司 阿戈美拉汀的制备方法、阿戈美拉汀晶形及其制备方法
CN102001959B (zh) * 2009-09-01 2014-07-02 北京本草天源药物研究院 一种药物晶体及其制备方法和用途
CN102050755B (zh) * 2009-10-29 2014-11-05 重庆医药工业研究院有限责任公司 阿戈美拉汀的晶型及其制备方法
CN101781226B (zh) * 2009-12-23 2012-03-28 天津泰普药品科技发展有限公司 阿戈美拉汀及其药物组合物
WO2011154140A2 (en) 2010-06-10 2011-12-15 Gador S.A. New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide and new crystalline form
CN102000583B (zh) * 2010-11-18 2012-08-15 烟台万华聚氨酯股份有限公司 一种氯化氢氧化制氯气的催化剂及其制备方法
CN102690209A (zh) * 2011-03-23 2012-09-26 上海医药工业研究院 阿戈美拉汀的混晶(形式-ⅷ)、其制备方法、应用和包含其的药物组合物
CN102690210A (zh) * 2011-03-23 2012-09-26 上海医药工业研究院 阿戈美拉汀的新晶型ⅶ、其制备方法、应用和包含其的药物组合物
PL2723714T3 (pl) * 2011-06-02 2018-02-28 CHINOIN Zrt. Nowe sposoby otrzymywania amidów prostaglandyn
FR2978916B1 (fr) 2011-08-10 2013-07-26 Servier Lab Composition pharmaceutique solide pour administration buccale d'agomelatine
EP2771312B1 (en) 2011-11-30 2017-05-31 ratiopharm GmbH Agomelatine-urea complex and crystalline forms thereof
CZ2012108A3 (en) 2012-02-15 2013-02-27 Zentiva Ks A method for the manufacture of a polymorphously stable pharmaceutical composition containing agomelatine
CN103360275B (zh) * 2012-03-30 2015-04-22 上海创诺制药有限公司 一种制备阿戈美拉汀ⅰ型晶体的方法
WO2014096373A1 (en) 2012-12-21 2014-06-26 Laboratorios Lesvi, S. L. Process for prepararing n-(2-(7-methoxy-1-naphthalenyl)ethyl) acetamide and solid forms thereof
FR3001894A1 (fr) 2013-02-08 2014-08-15 Servier Lab Composition pharmaceutique solide pour administration buccale d'agomelatine
EP2810647A1 (en) 2013-06-06 2014-12-10 Zentiva, a.s. Pharmaceutical formulations comprising agomelatine in the form of agomelatine co-crystal with an organic acid
HUE036989T2 (hu) 2013-06-06 2018-08-28 Zentiva Ks Agomelatin készítmény, amely agomelatint ko-kristály formájában tartalmaz
CZ2013621A3 (cs) 2013-08-13 2015-02-25 Zentiva, K.S. Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci
WO2015124496A1 (en) 2014-02-19 2015-08-27 Synthon B.V. Pharmaceutical composition comprising amorphous agomelatine
FR3033131B1 (fr) 2015-02-26 2017-11-17 Servitronique Glissiere pour ses systemes de reglage coulissants et procede d'assemblage
EP3075724B1 (en) 2015-03-31 2023-07-12 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Solid form of agomelatine
EP3466923A1 (en) 2017-10-09 2019-04-10 KRKA, d.d., Novo mesto Process for the preparation of agomelatine in crystalline form
EP3466413A1 (en) 2017-10-09 2019-04-10 KRKA, d.d., Novo mesto Pharmaceutical composition containing agomelatine and process for the preparation thereof
CN113952323A (zh) * 2021-12-10 2022-01-21 李甜 阿戈美拉汀在抑制Ube2c蛋白表达中的应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2658818B1 (fr) * 1990-02-27 1993-12-31 Adir Cie Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2866336B1 (fr) * 2004-02-13 2006-03-24 Servier Lab Nouveau procede de synthese du (7-methoxy-3,4-dihydro-1-naphtalenyl) acetonitrile et application a la synthese de l'agomelatine
FR2866335B1 (fr) * 2004-02-13 2006-05-26 Servier Lab Nouveau procede de synthese de l'agomelatine

Also Published As

Publication number Publication date
GT200600346A (es) 2007-02-28
EP1752443A1 (fr) 2007-02-14
AP2006003695A0 (en) 2006-08-31
CA2555115A1 (fr) 2007-02-03
AU2006203342A1 (en) 2007-02-22
NO336967B1 (no) 2015-12-07
AP2486A (en) 2012-10-03
IL177173A (en) 2011-10-31
FR2889523B1 (fr) 2007-12-28
JP4575337B2 (ja) 2010-11-04
ME02026B (me) 2012-11-06
AU2006203342B2 (en) 2012-07-19
SI1752443T1 (sl) 2012-10-30
ZA200606453B (en) 2007-12-27
SA06270255B1 (ar) 2010-06-13
EP1752443B1 (fr) 2012-07-11
CU20060153A7 (es) 2012-04-15
TWI359128B (en) 2012-03-01
TW200736199A (en) 2007-10-01
PL1752443T3 (pl) 2012-11-30
SG130110A1 (en) 2007-03-20
MY139902A (en) 2009-11-30
AR057715A1 (es) 2007-12-12
EP2277857A2 (fr) 2011-01-26
JP2007056017A (ja) 2007-03-08
HRP20120779T1 (hr) 2012-10-31
EP2277857A3 (fr) 2011-06-01
CN100448843C (zh) 2009-01-07
ECSP066715A (enExample) 2007-03-29
MA28451B1 (fr) 2007-03-01
CA2555115C (fr) 2013-12-10
DK1752443T3 (da) 2012-10-22
BRPI0603059A (pt) 2007-08-14
RS52423B (sr) 2013-02-28
CN1907958A (zh) 2007-02-07
FR2889523A1 (fr) 2007-02-09
IL177173A0 (en) 2006-12-10
MXPA06008789A (es) 2007-02-02
NZ548864A (en) 2008-03-28
EA011030B1 (ru) 2008-12-30
JO2793B1 (en) 2014-03-15
WO2007015004A2 (fr) 2007-02-08
EA200601273A1 (ru) 2007-02-27
WO2007015004A3 (fr) 2007-03-22
PT1752443E (pt) 2012-07-25
UA83720C2 (ru) 2008-08-11
HK1098128A1 (zh) 2007-07-13
CY1113011T1 (el) 2016-04-13
CR8529A (es) 2006-12-07
NO20063517L (no) 2007-02-05
ES2391406T3 (es) 2012-11-26

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