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
Authority
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
Other languages
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
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
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
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • A61P25/28—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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • 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)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (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
WO2006016904A2 (en) * 2004-04-14 2006-02-16 Uab Research Foundation Activators of hexosamine biosynthesis as inhibitors of injury induced by ischemia or hemorrhagic 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
EP2057171A4 (en) * 2006-08-31 2010-04-21 Univ Fraser Simon SELECTIVE GLYCOSIDASE INHIBITORS AND APPLICATIONS 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
WO2010012106A1 (en) 2008-08-01 2010-02-04 Simon Fraser University Selective glycosidase inhibitors and uses thereof
JP5687194B2 (ja) * 2008-08-01 2015-03-18 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インヒビターおよびその使用
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
US9120781B2 (en) * 2010-05-11 2015-09-01 Simon Fraser University Selective glycosidase inhibitors and uses thereof
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
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
US8901087B2 (en) * 2010-11-08 2014-12-02 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
WO2012061972A1 (en) * 2010-11-08 2012-05-18 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
WO2012061927A1 (en) 2010-11-08 2012-05-18 Alectos Therapeutics, Inc. 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
BR112013016179A2 (pt) * 2010-12-23 2018-07-10 Alectos Therapeutics Inc inibidores seletivos da glicosidase e usos dos mesmos.
WO2012126091A1 (en) * 2011-03-24 2012-09-27 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
US9718854B2 (en) 2011-03-31 2017-08-01 Alectos Therapeutics Inc. 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
WO2013000086A1 (en) 2011-06-27 2013-01-03 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
MX364602B (es) 2011-06-27 2019-05-02 Alectos Therapeutics Inc Inhibidores selectivos de glicosidasa y usos de los mismos.
EP2744338B1 (en) * 2011-08-18 2016-04-27 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
US8884023B2 (en) * 2011-08-25 2014-11-11 Merck Patent Gmbh Pyrano [3,2-D][1,3]thiazole as glycosidase inhibitors
CN104395323B (zh) * 2012-05-08 2017-08-01 默沙东公司 可透过性糖苷酶抑制剂及其用途
EP2890676B1 (en) 2012-08-31 2018-12-05 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
EP2890675A4 (en) 2012-08-31 2016-01-13 Alectos Therapeutics Inc GLYCOSIDASE INHIBITORS AND USES THEREOF
US9562066B2 (en) 2012-09-25 2017-02-07 University Of Pittsburgh-Of The Commonwealth System Of Higher Education Oral therapy of necrotizing enterocolitis
EP2914604A4 (en) 2012-10-31 2016-07-20 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
MX381417B (es) 2014-08-28 2025-03-12 Asceneuron Sa Inhibidores de glucosidasa.
US11261183B2 (en) 2016-02-25 2022-03-01 Asceneuron Sa Sulfoximine glycosidase inhibitors
JP6971999B2 (ja) 2016-02-25 2021-11-24 エースニューロン・ソシエテ・アノニム ピペラジン誘導体の酸付加塩
CN108884077A (zh) 2016-02-25 2018-11-23 阿森纽荣股份公司 糖苷酶抑制剂
JP2019506430A (ja) 2016-02-25 2019-03-07 エースニューロン・ソシエテ・アノニム グリコシダーゼ阻害剤
US11213525B2 (en) 2017-08-24 2022-01-04 Asceneuron Sa Linear glycosidase inhibitors
CA3110032A1 (en) 2018-08-22 2020-02-27 Asceneuron S.A. Succinate and fumarate acid addition salts of piperazine derivatives
WO2020039029A1 (en) 2018-08-22 2020-02-27 Asceneuron S. A. Spiro compounds as glycosidase inhibitors
US11795165B2 (en) 2018-08-22 2023-10-24 Asceneuron Sa Tetrahydro-benzoazepine glycosidase inhibitors
US12016852B2 (en) 2018-08-22 2024-06-25 Asceneuron Sa Pyrrolidine 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
EP1371733B1 (en) * 2001-03-14 2011-05-11 Denki Kagaku Kogyo Kabushiki Kaisha Process for producing hyaluronic acid or its derivative
WO2004103368A1 (en) * 2003-05-22 2004-12-02 The Hospital For Sick Children Treatment of tay sachs or sandhoff diseases by enhancing hexosaminidase activity
EP2057171A4 (en) * 2006-08-31 2010-04-21 Univ Fraser Simon SELECTIVE GLYCOSIDASE INHIBITORS AND APPLICATIONS THEREOF
WO2010012106A1 (en) * 2008-08-01 2010-02-04 Simon Fraser University Selective glycosidase inhibitors and uses thereof
JP5687194B2 (ja) * 2008-08-01 2015-03-18 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インヒビターおよびその使用
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
US9120781B2 (en) * 2010-05-11 2015-09-01 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
BR112013016179A2 (pt) * 2010-12-23 2018-07-10 Alectos Therapeutics Inc inibidores seletivos da glicosidase e usos dos mesmos.
WO2012126091A1 (en) * 2011-03-24 2012-09-27 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
US9718854B2 (en) * 2011-03-31 2017-08-01 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof

Also Published As

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

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Effective date: 20180301