WO2007136689A2 - Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor - Google Patents

Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor Download PDF

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Publication number
WO2007136689A2
WO2007136689A2 PCT/US2007/011810 US2007011810W WO2007136689A2 WO 2007136689 A2 WO2007136689 A2 WO 2007136689A2 US 2007011810 W US2007011810 W US 2007011810W WO 2007136689 A2 WO2007136689 A2 WO 2007136689A2
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WO
WIPO (PCT)
Prior art keywords
compound
formula
alkyl
salt
process according
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2007/011810
Other languages
English (en)
French (fr)
Other versions
WO2007136689A3 (en
Inventor
Tawfik Gharbaoui
Dipanjan Sengupta
Ashwin M. Krishnan
Nainesh Shah
Mark Macias
Ryan M. Hart
Edward A. Lally
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arena Pharmaceuticals Inc
Original Assignee
Arena Pharmaceuticals 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
Priority to KR1020087028020A priority Critical patent/KR101514846B1/ko
Priority to MX2013007579A priority patent/MX349156B/es
Priority to MX2008014622A priority patent/MX2008014622A/es
Priority to AU2007254255A priority patent/AU2007254255B2/en
Priority to EP20070794969 priority patent/EP2018372B1/en
Priority to ES07794969.1T priority patent/ES2543718T3/es
Priority to BRPI0712030-3A priority patent/BRPI0712030A2/pt
Priority to HK09101461.9A priority patent/HK1121453B/en
Priority to CN2007800145475A priority patent/CN101479248B/zh
Priority to NZ571829A priority patent/NZ571829A/en
Priority to NZ594353A priority patent/NZ594353A/xx
Priority to EA200870544A priority patent/EA016675B1/ru
Priority to US12/301,212 priority patent/US8481535B2/en
Priority to CA2646081A priority patent/CA2646081C/en
Application filed by Arena Pharmaceuticals Inc filed Critical Arena Pharmaceuticals Inc
Priority to JP2009511063A priority patent/JP5286254B2/ja
Publication of WO2007136689A2 publication Critical patent/WO2007136689A2/en
Publication of WO2007136689A3 publication Critical patent/WO2007136689A3/en
Priority to IL193822A priority patent/IL193822A/en
Anticipated expiration legal-status Critical
Priority to IL222340A priority patent/IL222340A/en
Priority to US13/935,329 priority patent/US9199940B2/en
Priority to US14/921,651 priority patent/US9783502B2/en
Priority to US15/700,670 priority patent/US20180186748A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P25/18—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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • 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
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives

Definitions

  • the present invention further provides processes for preparing a compound of Formula (VI) comprising reacting a compound of Formula (XTV):
  • the present invention further provides processes for preparing a compound of Formula (XIV) comprising reacting a compound of Formula (XV):
  • the compound of Formula (JJI) is added to a mixture containing the compound of Formula (II), the compound of Formula (A), and the trisubstituted phosphine.
  • additional portions of phosphine and/or additional portions of the compound of Formula (A) and/or additional portions of the compound of Formula (III) can be added after the initial reacting.
  • the solvent is an alcohol such as ethanol, n-propanol, isopropanol, n-butanol and the like. 5 In some embodiments, the solvent is isopropanol.
  • the reacting is carried out at a temperature of about -10 0 C to about 25 0 C.
  • the amine is added in situ after the formation of an intermediate of Formula (XII):
  • R 1 is methoxy
  • compositions of the invention include Compound 7 Form I and a pharmaceutically acceptable carrier.
  • the present invention further provides methods of treating a parasomnia comprising administering to a patient a therapeutically effective amount of a salt or a crystalline form as described herein.
  • One aspect of the present invention pertains to use of a salt or a crystalline form of the present invention for the manufacture of a medicament for treating a diabetic-related disorder.
  • One aspect of the present invention pertains to use of a salt or a crystalline form of the present invention for the manufacture of a medicament for treating progressive multifocal 25 leukoencephalopathy.
  • cycloalkyl 25 cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcarnyl, adamantyl, and the like.
  • moieties that have one or more aromatic rings fused with (i.e., having a bond in common with) the cycloalkyl ring, for example, benzo derivatives of pentane, hexane, and the like.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Addiction (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/US2007/011810 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor Ceased WO2007136689A2 (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
US12/301,212 US8481535B2 (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
MX2008014622A MX2008014622A (es) 2006-05-18 2007-05-17 Formas cristalinas y procesos para la preparacion de fenil-pirazoles utiles como moduladores del receptor de serotonina 5-ht2a.
AU2007254255A AU2007254255B2 (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
EP20070794969 EP2018372B1 (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor
ES07794969.1T ES2543718T3 (es) 2006-05-18 2007-05-17 Formas cristalinas y procesos para la preparación de fenil-pirazoles útiles como moduladores del receptor de serotonina 5-HT2A
BRPI0712030-3A BRPI0712030A2 (pt) 2006-05-18 2007-05-17 formas cristalinas e processos para preparaÇço de fenil-pirazàis éteis como moduladores dos receptores de serotonina 5-h-t2a
MX2013007579A MX349156B (es) 2006-05-18 2007-05-17 Formas cristalinas y procesos para la preparacion de fenil-pirazoles utiles como moduladores del receptor de serotonina 5-ht2a.
CN2007800145475A CN101479248B (zh) 2006-05-18 2007-05-17 用作5-ht2a血清素受体调节剂的苯基-吡唑的晶型和其制备方法
NZ571829A NZ571829A (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
NZ594353A NZ594353A (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
EA200870544A EA016675B1 (ru) 2006-05-18 2007-05-17 Способы получения фенилпиразолов и кристаллическая форма производного фенилпиразола
KR1020087028020A KR101514846B1 (ko) 2006-05-18 2007-05-17 ５-ｈｔ２ａ 세로토닌 수용체의 조절인자로서 유용한 페닐-피라졸의 결정질 형태 및 그의 제조 방법
HK09101461.9A HK1121453B (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor
CA2646081A CA2646081C (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor
JP2009511063A JP5286254B2 (ja) 2006-05-18 2007-05-17 ５−ｈｔ２ａセロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法
IL193822A IL193822A (en) 2006-05-18 2008-09-01 Forms of crystals and processes for the preparation of phenyl-pyrazole are effective as 5-a2ht serotonin receptor modulators
IL222340A IL222340A (en) 2006-05-18 2012-10-10 Forms of crystals and processes for the preparation of phenyl-pyrazole are effective as 5-a2ht serotonin receptor modulators
US13/935,329 US9199940B2 (en) 2006-05-18 2013-07-03 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
US14/921,651 US9783502B2 (en) 2006-05-18 2015-10-23 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
US15/700,670 US20180186748A1 (en) 2006-05-18 2017-09-11 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulaters of the 5-ht2a serotonin receptor

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US80178906P 2006-05-18 2006-05-18
US60/801,789 2006-05-18
US92131807P 2007-04-02 2007-04-02
US60/921,318 2007-04-02

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/301,212 A-371-Of-International US8481535B2 (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
US13/935,329 Division US9199940B2 (en) 2006-05-18 2013-07-03 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor

Publications (2)

Publication Number Publication Date
WO2007136689A2 true WO2007136689A2 (en) 2007-11-29
WO2007136689A3 WO2007136689A3 (en) 2008-01-10

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PCT/US2007/011810 Ceased WO2007136689A2 (en) 2006-05-18 2007-05-17 Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor

Country Status (16)

Country Link
US (4) US8481535B2 (enExample)
EP (2) EP2527329A1 (enExample)
JP (1) JP5286254B2 (enExample)
KR (1) KR101514846B1 (enExample)
CN (1) CN102827081A (enExample)
AU (1) AU2007254255B2 (enExample)
BR (1) BRPI0712030A2 (enExample)
CA (1) CA2646081C (enExample)
EA (1) EA016675B1 (enExample)
ES (1) ES2543718T3 (enExample)
IL (2) IL193822A (enExample)
MX (2) MX2008014622A (enExample)
MY (1) MY154962A (enExample)
NZ (2) NZ594353A (enExample)
SG (1) SG171681A1 (enExample)
WO (1) WO2007136689A2 (enExample)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011075596A1 (en) 2009-12-18 2011-06-23 Arena Pharmaceuticals, Inc. Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto
US8481535B2 (en) 2006-05-18 2013-07-09 Arena Pharmaceuticals, Inc. Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor
US8664258B2 (en) 2006-05-18 2014-03-04 Arena Pharmaceuticals, Inc. Primary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
US8785441B2 (en) 2004-11-19 2014-07-22 Arena Pharmaceuticals, Inc. 3-phenyl-pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
US9221755B2 (en) 2006-05-18 2015-12-29 Arena Pharmaceuticals, Inc. Ethers, secondary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
US9732039B2 (en) 2006-10-03 2017-08-15 Arena Pharmeceuticals, Inc. Pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
US9745270B2 (en) 2008-10-28 2017-08-29 Arena Pharmaceuticals, Inc. Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto
US9801856B2 (en) 2008-10-28 2017-10-31 Arena Pharmaceuticals, Inc. Composition of a 5-HT2A serotonin receptor modulator useful for the treatment of disorders related thereto
US10022355B2 (en) 2015-06-12 2018-07-17 Axovant Sciences Gmbh Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of REM sleep behavior disorder
US10034859B2 (en) 2015-07-15 2018-07-31 Axovant Sciences Gmbh Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease
US10058549B2 (en) 2007-08-15 2018-08-28 Arena Pharmaceuticals, Inc. Imidazo[1,2-α]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
US10787437B2 (en) 2008-04-02 2020-09-29 Arena Pharmaceuticals, Inc. Processes for the preparation of pyrazole derivatives useful as modulators of the 5-HT2A serotonin receptor

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HRP20060100T3 (en) 2003-07-22 2007-03-31 Arena Pharmaceuticals Inc Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related thereto
CA2797533A1 (en) * 2010-04-27 2011-11-10 Calcimedica, Inc. Compounds that modulate intracellular calcium

Citations (3)

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Publication number Priority date Publication date Assignee Title
WO2004058722A1 (en) 2002-12-24 2004-07-15 Arena Pharmaceuticals, Inc. Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a
WO2005012254A1 (en) 2003-07-22 2005-02-10 Arena Pharmaceuticals, Inc. Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related therto
WO2006055734A2 (en) 2004-11-19 2006-05-26 Arena Pharmaceuticals, Inc. 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto

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