CA2599843C - Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof - Google Patents

Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof Download PDF

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Publication number
CA2599843C
CA2599843C CA2599843A CA2599843A CA2599843C CA 2599843 C CA2599843 C CA 2599843C CA 2599843 A CA2599843 A CA 2599843A CA 2599843 A CA2599843 A CA 2599843A CA 2599843 C CA2599843 C CA 2599843C
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CA
Canada
Prior art keywords
thiazoline
dideoxy
glucopyranoso
pyrano
thiazole
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.)
Expired - Fee Related
Application number
CA2599843A
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English (en)
French (fr)
Other versions
CA2599843A1 (en
Inventor
Matthew Macauley
David Vocadlo
Garrett Whitworth
Keith Stubbs
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.)
Simon Fraser University
Original Assignee
Simon Fraser University
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Filing date
Publication date
Application filed by Simon Fraser University filed Critical Simon Fraser University
Priority to CA2819464A priority Critical patent/CA2819464A1/en
Publication of CA2599843A1 publication Critical patent/CA2599843A1/en
Application granted granted Critical
Publication of CA2599843C publication Critical patent/CA2599843C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • A61P25/28Drugs 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
    • 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
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2599843A 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof Expired - Fee Related CA2599843C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2819464A CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US65687805P 2005-03-01 2005-03-01
US60/656,878 2005-03-01
PCT/CA2006/000300 WO2006092049A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2819464A Division CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Publications (2)

Publication Number Publication Date
CA2599843A1 CA2599843A1 (en) 2006-09-08
CA2599843C true CA2599843C (en) 2013-08-27

Family

ID=36940808

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2599843A Expired - Fee Related CA2599843C (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof
CA2819464A Abandoned CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2819464A Abandoned CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Country Status (7)

Country Link
US (1) US20080287375A1 (enExample)
EP (2) EP1869060B1 (enExample)
JP (1) JP5154954B2 (enExample)
CN (1) CN101208352B (enExample)
AU (1) AU2006220187B2 (enExample)
CA (2) CA2599843C (enExample)
WO (1) WO2006092049A1 (enExample)

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080166323A1 (en) * 2004-04-14 2008-07-10 Uab Research Foundation Activators of Hexosamine Biosynthesis as Inhibitors of Injury Induced by Ischemia or Hermorrhagic Shock
CN101595111A (zh) * 2006-08-31 2009-12-02 西蒙·弗雷瑟大学 选择性糖苷酶抑制剂及其用途
US8334310B2 (en) 2006-08-31 2012-12-18 Simon Fraser University Selective glycosidase inhibitors and uses thereof
GB0622702D0 (en) * 2006-11-15 2006-12-27 Univ Dundee Selective glycosidase inhibitors
US8518903B2 (en) 2007-04-19 2013-08-27 University of Pittsburgh—of the Commonwealth System of Higher Education Use of toll-like receptor-9 agonists
AU2009276222B2 (en) 2008-08-01 2015-03-05 Simon Fraser University Selective glycosidase inhibitors and uses thereof
US9079868B2 (en) * 2008-08-01 2015-07-14 Simon Fraser University Selective glycosidase inhibitors and uses thereof
JP2012502884A (ja) * 2008-09-16 2012-02-02 サイモン フレイザー ユニバーシティ 選択的グリコシダーゼ阻害剤およびその使用
EP2569291B1 (en) 2010-05-11 2016-04-06 Simon Fraser University Selective glycosidase inhibitors and uses thereof
US10668092B2 (en) 2010-09-24 2020-06-02 The John Hopkins University Compositions and methods for treatment of inflammatory disorders
US9072760B2 (en) 2010-09-24 2015-07-07 University of Pittsburgh—of the Commonwealth System of Higher Education TLR4 inhibitors for the treatment of human infectious and inflammatory disorders
WO2012040719A2 (en) * 2010-09-24 2012-03-29 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Novel tlr4 inhibitors for the treatment of human infectious and inflammatory disorders
WO2012061927A1 (en) 2010-11-08 2012-05-18 Alectos Therapeutics, Inc. Selective glycosidase inhibitors and uses thereof
WO2012061972A1 (en) * 2010-11-08 2012-05-18 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
US8901087B2 (en) * 2010-11-08 2014-12-02 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
TW201249848A (en) 2010-11-08 2012-12-16 Merck Sharp & Dohme Selective glycosidase inhibitors and uses thereof
WO2012088425A2 (en) 2010-12-22 2012-06-28 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Gap junction-enhancing agents for treatment of necrotizing enterocolitis and inflammatory bowel disease
CA2822493C (en) 2010-12-23 2018-11-20 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
US8927507B2 (en) 2011-03-24 2015-01-06 Ernest J. McEachern Selective glycosidase inhibitors and uses thereof
WO2012129802A1 (en) * 2011-03-31 2012-10-04 Alectos Therapeutics Inc. Pyrano[3,2-d]thiazol derivatives and uses as selective glycosidase inhibitors thereof
WO2012129651A1 (en) 2011-03-31 2012-10-04 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
WO2013000085A1 (en) 2011-06-27 2013-01-03 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
CN103889996B (zh) * 2011-06-27 2016-02-03 阿列科托斯治疗有限公司 选择性糖苷酶抑制剂及其用途
US9701693B2 (en) 2011-06-27 2017-07-11 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
WO2013025452A1 (en) * 2011-08-18 2013-02-21 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
SG2014009617A (en) * 2011-08-25 2014-05-29 Merck Patent Gmbh Pyrano [3, 2 - d] [1, 3] thiazole as glycosidase inhibitors
RU2707292C2 (ru) * 2012-05-08 2019-11-26 Мерк Шарп И Доум Корп. Проницаемые ингибиторы гликозидазы и их применения
US9670195B2 (en) 2012-08-31 2017-06-06 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
WO2014032188A1 (en) 2012-08-31 2014-03-06 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
WO2014052453A1 (en) 2012-09-25 2014-04-03 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Oral therapy of necrotizing enterocolitis
WO2014067003A1 (en) 2012-10-31 2014-05-08 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
WO2014100934A1 (en) 2012-12-24 2014-07-03 Merck Sharp & Dohme Corp. Glycosidase inhibitors and uses thereof
WO2014171206A1 (ja) * 2013-04-17 2014-10-23 Yuasa Tomoyuki 糖尿病治療薬の新規なスクリーニング方法
MA53944A (fr) 2014-08-28 2021-08-25 Asceneuron Sa Inhibiteurs de la glycosidase
US11261183B2 (en) 2016-02-25 2022-03-01 Asceneuron Sa Sulfoximine glycosidase inhibitors
MA43677A (fr) 2016-02-25 2018-11-28 Asceneuron Sa Inhibiteurs de glycosidases
WO2017144637A1 (en) 2016-02-25 2017-08-31 Asceneuron S. A. Acid addition salts of piperazine derivatives
CN108884078A (zh) 2016-02-25 2018-11-23 阿森纽荣股份公司 糖苷酶抑制剂
US11213525B2 (en) 2017-08-24 2022-01-04 Asceneuron Sa Linear glycosidase inhibitors
US12195455B2 (en) 2018-08-22 2025-01-14 Asceneuron Sa Succinate and fumarate acid addition salts of piperazine derivatives
WO2020039027A1 (en) 2018-08-22 2020-02-27 Asceneuron S. A. Pyrrolidine glycosidase inhibitors
US11731972B2 (en) 2018-08-22 2023-08-22 Asceneuron Sa Spiro compounds as glycosidase inhibitors
US11795165B2 (en) 2018-08-22 2023-10-24 Asceneuron Sa Tetrahydro-benzoazepine glycosidase inhibitors
CN114524854B (zh) * 2022-02-25 2023-05-26 中国农业大学 一种糖基芳香环碳苷衍生物及其制备方法与应用
WO2024083820A1 (en) 2022-10-18 2024-04-25 Institut National de la Santé et de la Recherche Médicale Method and composition for determining the level of o-glcnacylation in horses
CN116376875B (zh) * 2023-03-03 2024-02-23 云南师范大学 耐热性提高的n-乙酰氨基葡萄糖苷酶突变体及其应用
CN116555229B (zh) * 2023-05-25 2024-09-20 云南师范大学 N-乙酰氨基葡萄糖苷酶突变体、重组表达载体及菌和应用
CN118086249B (zh) * 2024-01-24 2024-12-06 云南师范大学 一种协同提高酶活和热稳定性的n-乙酰氨基葡萄糖苷酶突变体及其制备与应用

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9818732D0 (en) * 1998-08-27 1998-10-21 Univ Portsmouth Collection of compounds
US6774140B1 (en) * 1999-05-11 2004-08-10 The Scripps Research Institute Iminocyclitol inhibitors of hexoaminidase and glycosidase
WO2002072860A1 (en) * 2001-03-14 2002-09-19 Denki Kagaku Kogyo Kabushiki Kaisha Process for producing hyaluronic acid or its derivative
US20070066543A1 (en) * 2003-05-22 2007-03-22 The Hospital For Sick Children Treatment of tay sachs or sandhoff diseases by enhancing hexosaminidase activity
US8334310B2 (en) * 2006-08-31 2012-12-18 Simon Fraser University Selective glycosidase inhibitors and uses thereof
US9079868B2 (en) * 2008-08-01 2015-07-14 Simon Fraser University Selective glycosidase inhibitors and uses thereof
AU2009276222B2 (en) * 2008-08-01 2015-03-05 Simon Fraser University Selective glycosidase inhibitors and uses thereof
JP2012502884A (ja) * 2008-09-16 2012-02-02 サイモン フレイザー ユニバーシティ 選択的グリコシダーゼ阻害剤およびその使用
EP2569291B1 (en) * 2010-05-11 2016-04-06 Simon Fraser University Selective glycosidase inhibitors and uses thereof
WO2012061927A1 (en) * 2010-11-08 2012-05-18 Alectos Therapeutics, Inc. Selective glycosidase inhibitors and uses thereof
CA2822493C (en) * 2010-12-23 2018-11-20 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
US8927507B2 (en) * 2011-03-24 2015-01-06 Ernest J. McEachern Selective glycosidase inhibitors and uses thereof
WO2012129651A1 (en) * 2011-03-31 2012-10-04 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof

Also Published As

Publication number Publication date
EP1869060B1 (en) 2012-08-15
AU2006220187B2 (en) 2012-11-08
CA2599843A1 (en) 2006-09-08
CA2819464A1 (en) 2006-09-08
JP5154954B2 (ja) 2013-02-27
US20080287375A1 (en) 2008-11-20
CN101208352B (zh) 2013-08-07
JP2008531604A (ja) 2008-08-14
EP1869060A1 (en) 2007-12-26
EP1869060A4 (en) 2009-08-12
WO2006092049A1 (en) 2006-09-08
CN101208352A (zh) 2008-06-25
AU2006220187A1 (en) 2006-09-08
EP2436687A1 (en) 2012-04-04

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MKLA Lapsed

Effective date: 20180301

MKLA Lapsed

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Effective date: 20180301