AU2015253464B2 - Processes and intermediates for the preparation of a PDE10 inhibitor - Google Patents

Processes and intermediates for the preparation of a PDE10 inhibitor Download PDF

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Publication number
AU2015253464B2
AU2015253464B2 AU2015253464A AU2015253464A AU2015253464B2 AU 2015253464 B2 AU2015253464 B2 AU 2015253464B2 AU 2015253464 A AU2015253464 A AU 2015253464A AU 2015253464 A AU2015253464 A AU 2015253464A AU 2015253464 B2 AU2015253464 B2 AU 2015253464B2
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metal
formula
compound
group
converting
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AU2015253464A1 (en
Inventor
Elisabeth C.A. Brot
Neil S. Cutshall
Jennifer Lynn Gage
Marco Jonas
Thomas L. Little
Wayne Douglas Luke
Michael James Mcdermott
Karl E. Reineke
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Omeros Corp
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Omeros Medical Systems Inc
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    • 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
    • A61K31/4245—Oxadiazoles
    • 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
    • A61K31/433—Thidiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/02—Magnesium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
AU2015253464A 2014-04-28 2015-04-24 Processes and intermediates for the preparation of a PDE10 inhibitor Active AU2015253464B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201461985400P 2014-04-28 2014-04-28
US61/985,400 2014-04-28
PCT/US2015/027647 WO2015167969A1 (en) 2014-04-28 2015-04-24 Processes and intermediates for the preparation of a pde10 inhibitor

Publications (2)

Publication Number Publication Date
AU2015253464A1 AU2015253464A1 (en) 2016-10-27
AU2015253464B2 true AU2015253464B2 (en) 2018-11-22

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AU2015253464A Active AU2015253464B2 (en) 2014-04-28 2015-04-24 Processes and intermediates for the preparation of a PDE10 inhibitor

Country Status (13)

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US (2) US9650368B2 (enExample)
EP (1) EP3137462B1 (enExample)
JP (1) JP6474430B2 (enExample)
KR (1) KR102496552B1 (enExample)
CN (1) CN106459026B (enExample)
AU (1) AU2015253464B2 (enExample)
BR (1) BR112016025287B1 (enExample)
CA (1) CA2946756C (enExample)
ES (1) ES2723437T3 (enExample)
IL (1) IL248585B (enExample)
NZ (2) NZ630810A (enExample)
RU (1) RU2718863C2 (enExample)
WO (1) WO2015167969A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ601967A (en) * 2010-03-12 2015-03-27 Omeros Corp Pde10 inhibitors and related compositions and methods
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor
CA3003611C (en) 2015-11-04 2022-11-01 Omeros Corporation Solid state forms of a pde10 inhibitor

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060074102A1 (en) * 2004-05-14 2006-04-06 Kevin Cusack Kinase inhibitors as therapeutic agents
US7449486B2 (en) * 2004-10-19 2008-11-11 Array Biopharma Inc. Mitotic kinesin inhibitors and methods of use thereof
US20110224202A1 (en) * 2010-03-12 2011-09-15 Omeros Corporation Pde10 inhibitors and related compositions and methods
US8278327B2 (en) * 2006-11-21 2012-10-02 Omeros Corporation PDE10 inhibitors and related compositions and methods

Family Cites Families (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK178590D0 (da) 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
PT100905A (pt) 1991-09-30 1994-02-28 Eisai Co Ltd Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem
DK0672031T3 (da) 1992-12-02 2003-06-10 Pfizer Catecholdiethere som selektive PDE IV-inhibitorer
DE4323192A1 (de) 1993-07-10 1995-01-12 Basf Ag Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen
DE4325846C1 (de) 1993-07-31 1995-01-19 Herberts Gmbh Verwendung von Furan-modifizierten aromatischen Pinakolderivaten als Initiatoren und Furan-modifizierte aromatische Pinakolderivate als solche
DE4343286A1 (de) 1993-12-17 1995-06-22 Hoechst Ag Heteroaromatische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
DE4409501A1 (de) 1994-03-19 1995-09-21 Didier Werke Ag Verschleißfutter eines Schachtofens und Stein hierfür
JP3056788B2 (ja) 1994-06-24 2000-06-26 ユーロ−セルティーク，エス．エイ． ホスホジエステラーゼｉｖの阻害化合物および阻害方法
US5789434A (en) 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
TW424087B (en) 1995-04-06 2001-03-01 Janssen Pharmaceutica Nv 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives
TW332201B (en) 1995-04-06 1998-05-21 Janssen Pharmaceutica Nv 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives
US6037370A (en) 1995-06-08 2000-03-14 Vertex Pharmaceuticals Incorporated Methods and compositions for stimulating neurite growth
EP1170009B1 (en) 1996-01-22 2004-04-07 Fujisawa Pharmaceutical Co., Ltd. Thiazolybenzofuran derivatives and their use as SRS-A and leukotiene antagonists
AU4015497A (en) 1996-08-26 1998-03-19 Byk Gulden Lomberg Chemische Fabrik Gmbh Thiazole derivatives useful as selective inhibitors of pde-iv
JPH1087543A (ja) 1996-09-17 1998-04-07 Chisso Corp アルコキシベンゼン誘導体、液晶組成物および液晶表示素子
US6548490B1 (en) 1997-10-28 2003-04-15 Vivus, Inc. Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
WO1999045914A1 (en) 1998-03-13 1999-09-16 Maruho Kabushikikaisha Alkyl amine derivative and local anesthetic agent using the same
GB9807354D0 (en) 1998-04-07 1998-06-03 Glaxo Group Ltd Antiviral compound
SE9804212D0 (sv) 1998-12-04 1998-12-04 Astra Pharma Prod Compounds
TR200102817T2 (tr) 1999-03-12 2002-05-21 Boehringer Ingelheim Pharmaceuticals, Inc. Antiinflamatuar ajanlar olarak faydalı bileşikler
US7141593B1 (en) 1999-06-04 2006-11-28 Abbott Laboratories Pharmaceutical formulations
GB9929552D0 (en) 1999-12-14 2000-02-09 Proteus Molecular Design Compounds
JP2004511434A (ja) 2000-06-15 2004-04-15 ファルマシア・コーポレーション インテグリン受容体アンタゴニストとしてのヘテロアリールアルカン酸
US20030032579A1 (en) 2001-04-20 2003-02-13 Pfizer Inc. Therapeutic use of selective PDE10 inhibitors
DE60209704T2 (de) 2001-05-22 2006-11-16 Pfizer Products Inc., Groton Neue kristallforme von azithromycin
AU2003229912A1 (en) * 2002-04-18 2003-11-03 Avecia Limited Prepation of a conjugated molecule and materials for use therein
US6821502B2 (en) 2002-06-12 2004-11-23 Chevron U.S.A. Inc. Method of making aluminum-containing zeolite with IFR structure
US20050272036A1 (en) 2002-07-27 2005-12-08 Barton Peter J Ketones
AU2003275493A1 (en) 2002-10-08 2004-05-04 The Scripps Research Institute Inhibitors of fatty acid amide hydrolase
AU2003288352A1 (en) 2002-10-30 2004-06-07 Centre National De La Recherche Scientifique (Cnrs) Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses
TW200410921A (en) 2002-11-25 2004-07-01 Hoffmann La Roche Mandelic acid derivatives
US20060040986A1 (en) 2002-12-06 2006-02-23 Kowa Co., Ltd. Erythropoietin production accelerator
BR0317600A (pt) 2002-12-20 2005-11-29 Pharmacia Corp ácidos heteroarilalcanóicos como derivados de antagonistas de receptor de integrina
WO2004071509A1 (ja) 2003-02-12 2004-08-26 Nippon Chemiphar Co., Ltd. オリゴデンドロサイト分化促進剤
US7226930B2 (en) 2003-04-18 2007-06-05 Memory Pharmaceutical Corporation Phosphodiesterase 4 inhibitors
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
NZ550114A (en) 2004-04-20 2011-02-25 Transtech Pharma Inc Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators
US7351833B2 (en) 2004-07-23 2008-04-01 Abbott Laboratories (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate
US8436176B2 (en) 2004-12-30 2013-05-07 Medicis Pharmaceutical Corporation Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine
WO2006072828A2 (en) 2005-01-07 2006-07-13 Pfizer Products Inc. Heteroaromatic quinoline compounds and their use as pde10 inhibitors
CN101384183B (zh) 2005-02-04 2012-07-04 西诺米克斯公司 包含连接有杂芳基部分的化合物及其作为用于食物组合物的新型鲜味调节剂、促味剂和味觉增强剂的应用
US20060252807A1 (en) 2005-04-22 2006-11-09 Kalypsys, Inc. Novel ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders
UA91546C2 (uk) 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ
MY152185A (en) 2005-06-10 2014-08-29 Novartis Ag Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation
CA2617788A1 (en) 2005-08-04 2007-02-15 Apogee Biotechnology Corporation Sphingosine kinase inhibitors and methods of their use
PT1924585E (pt) 2005-08-29 2012-01-19 Sanofi Aventis Us Llc Nova forma cristalina de um derivado de piridazino[4,5-b]indole
DE602006019822D1 (de) 2005-09-13 2011-03-10 Sicor Inc Reines rocuroniumbromid
TWI330639B (en) 2005-11-15 2010-09-21 Otsuka Pharma Co Ltd Oxazole compound and pharmaceutical composition
EP1968946A4 (en) 2005-12-23 2010-05-05 Astrazeneca Ab IMIDAZOLE AS MODULATORS OF THE GABA B RECEPTOR
JP2009535394A (ja) 2006-05-02 2009-10-01 ファイザー・プロダクツ・インク Ｐｄｅ１０阻害剤としての二環式ヘテロアリール化合物
US20080090834A1 (en) 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
JP2010502736A (ja) 2006-09-08 2010-01-28 オレ・ファーマシューティカルズ・インコーポレーテッド 消化管の炎症を低減または軽減するための方法
UA99600C2 (en) 2006-09-25 2012-09-10 ПиТиСи ТЕРАПЬЮТИКС, ИНК. Crystalline forms of 3-[5-(2-fhjorophenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid
KR20090064400A (ko) 2006-09-28 2009-06-18 머크 앤드 캄파니 인코포레이티드 Ｈｄａｃ 억제제 및 킬레이트화 가능한 금속 화합물 및 금속-ｈｄａｃ 억제제 킬레이트 착물의 약제학적 조성물
US20090253918A1 (en) 2006-10-02 2009-10-08 Janssen Pharmaceuticals, N.V. Novel intermediate for glyt1 inhibitor
US7837978B2 (en) 2006-10-13 2010-11-23 Chevron U.S.A. Inc. Process for preparing aluminum-containing molecular sieve SSZ-26
EP2083819B1 (en) 2006-11-21 2017-02-22 Omeros Corporation Pde10 inhibitors and related compositions and methods
PE20081506A1 (es) 2006-12-12 2008-12-09 Infinity Discovery Inc Formulaciones de ansamicina
WO2009008906A2 (en) 2007-02-06 2009-01-15 The Trustees Of The University Of Pennsylvania Therapeutic compounds for blocking dna synthesis of pox viruses
EP2160394A1 (en) 2007-05-22 2010-03-10 Ultimorphix Technologies B.v. Tenofovir disoproxil hemi-fumaric acid co-crystal
EP2017264A1 (de) 2007-07-16 2009-01-21 Bayer Cropscience Ag Substituierte Phenylpropargylverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2009049022A1 (en) 2007-10-10 2009-04-16 Ore Pharmaceuticals Inc. Method for treatment of pancreatitis
TW200944520A (en) 2008-01-29 2009-11-01 Glaxo Group Ltd Spiro compounds as NPY Y5 receptor antagonists
WO2009143178A2 (en) 2008-05-20 2009-11-26 Omeros Corporation Pde10 inhibitors and related compositions and methods
TWI501965B (zh) 2008-06-20 2015-10-01 Lundbeck & Co As H 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物
EP2310016B1 (en) 2008-08-05 2017-10-04 Omeros Corporation Pde10 inhibitors and related compositions and methods
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060074102A1 (en) * 2004-05-14 2006-04-06 Kevin Cusack Kinase inhibitors as therapeutic agents
US7449486B2 (en) * 2004-10-19 2008-11-11 Array Biopharma Inc. Mitotic kinesin inhibitors and methods of use thereof
US8278327B2 (en) * 2006-11-21 2012-10-02 Omeros Corporation PDE10 inhibitors and related compositions and methods
US20110224202A1 (en) * 2010-03-12 2011-09-15 Omeros Corporation Pde10 inhibitors and related compositions and methods

Also Published As

Publication number Publication date
BR112016025287B1 (pt) 2022-10-11
ES2723437T3 (es) 2019-08-27
KR102496552B1 (ko) 2023-02-06
US9650368B2 (en) 2017-05-16
RU2718863C2 (ru) 2020-04-15
RU2016146118A3 (enExample) 2018-12-24
NZ630810A (en) 2016-03-31
CN106459026B (zh) 2019-07-05
US20160024069A1 (en) 2016-01-28
JP2017513885A (ja) 2017-06-01
NZ716494A (en) 2017-07-28
CN106459026A (zh) 2017-02-22
WO2015167969A1 (en) 2015-11-05
KR20160147275A (ko) 2016-12-22
EP3137462B1 (en) 2019-01-30
JP6474430B2 (ja) 2019-02-27
EP3137462A1 (en) 2017-03-08
CA2946756A1 (en) 2015-11-05
IL248585B (en) 2020-03-31
BR112016025287A2 (pt) 2017-08-15
RU2016146118A (ru) 2018-05-30
EP3137462A4 (en) 2017-12-27
IL248585A0 (en) 2016-12-29
US20180057484A1 (en) 2018-03-01
AU2015253464A1 (en) 2016-10-27
CA2946756C (en) 2022-03-29

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