CA2159988C - Novel deoxygalactonojirimycin derivatives - Google Patents

Novel deoxygalactonojirimycin derivatives Download PDF

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Publication number
CA2159988C
CA2159988C CA002159988A CA2159988A CA2159988C CA 2159988 C CA2159988 C CA 2159988C CA 002159988 A CA002159988 A CA 002159988A CA 2159988 A CA2159988 A CA 2159988A CA 2159988 C CA2159988 C CA 2159988C
Authority
CA
Canada
Prior art keywords
dgj
dnj
glycolipid
cells
alkyl
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
CA002159988A
Other languages
English (en)
French (fr)
Other versions
CA2159988A1 (en
Inventor
Frances M. Platt
Gabrielle R. Neises
Raymond A. Dwek
Terry D. Butters
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.)
GD Searle LLC
Monsanto Co
Original Assignee
GD Searle LLC
Monsanto Co
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 claimed from US08/061,645 external-priority patent/US5399567A/en
Application filed by GD Searle LLC, Monsanto Co filed Critical GD Searle LLC
Publication of CA2159988A1 publication Critical patent/CA2159988A1/en
Application granted granted Critical
Publication of CA2159988C publication Critical patent/CA2159988C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/13—Amines
    • A61K31/131—Amines acyclic
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
CA002159988A 1993-05-13 1994-05-11 Novel deoxygalactonojirimycin derivatives Expired - Fee Related CA2159988C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US08/061,645 US5399567A (en) 1993-05-13 1993-05-13 Method of treating cholera
US08/061,645 1993-05-13
US08/102,654 1993-08-05
US08/102,654 US6291657B1 (en) 1993-05-13 1993-08-05 Deoxygalactonojirimycin derivatives
PCT/US1994/004974 WO1994026714A1 (en) 1993-05-13 1994-05-11 Novel deoxygalactonojirimycin derivatives

Publications (2)

Publication Number Publication Date
CA2159988A1 CA2159988A1 (en) 1994-11-24
CA2159988C true CA2159988C (en) 2007-01-09

Family

ID=26741316

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002159988A Expired - Fee Related CA2159988C (en) 1993-05-13 1994-05-11 Novel deoxygalactonojirimycin derivatives

Country Status (11)

Country Link
US (3) US6291657B1 (enExample)
EP (1) EP0698012B1 (enExample)
JP (1) JP3636363B2 (enExample)
AT (1) ATE148456T1 (enExample)
AU (1) AU6783294A (enExample)
CA (1) CA2159988C (enExample)
DE (1) DE69401658T2 (enExample)
DK (1) DK0698012T3 (enExample)
ES (1) ES2097653T3 (enExample)
GR (1) GR3022554T3 (enExample)
WO (1) WO1994026714A1 (enExample)

Families Citing this family (39)

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US5798366A (en) * 1993-05-13 1998-08-25 Monsanto Company Method for treatment of CNS-involved lysosomal storage diseases
US6465488B1 (en) 1997-12-11 2002-10-15 Chancellor, Masters & Scholars Of The University Of Oxford Inhibition of glycolipid biosynthesis
US6274597B1 (en) * 1998-06-01 2001-08-14 Mount Sinai School Of Medicine Of New York University Method of enhancing lysosomal α-Galactosidase A
AU1734600A (en) * 1998-11-17 2000-06-05 Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The Identification of glycosphingolipids that promote hiv-1 entry into cells
US6610703B1 (en) 1998-12-10 2003-08-26 G.D. Searle & Co. Method for treatment of glycolipid storage diseases
GB0100889D0 (en) * 2001-01-12 2001-02-21 Oxford Glycosciences Uk Ltd Compounds
US20050032841A1 (en) * 1999-04-20 2005-02-10 Steven Walkley Therapeutic compositions and methods of treating glycolipid storage related disorders
GB9909066D0 (en) * 1999-04-20 1999-06-16 Oxford Glycosciences Uk Ltd Therapies
ATE234626T1 (de) 1999-07-26 2003-04-15 Searle & Co Verwendung von langkettigen n-alkyl derivaten von deoxynojirimycin mit glucocerebrosidase enzyme zur herstellung eines medikaments zur behandlung von mit glykolipiden akkumulation zusammenhängenden krankheiten
US7256005B2 (en) 1999-08-10 2007-08-14 The Chancellor, Masters And Scholars Of The University Of Oxford Methods for identifying iminosugar derivatives that inhibit HCV p7 ion channel activity
US7816560B1 (en) 1999-08-10 2010-10-19 Thomas Jefferson University Long chain n-alkyl compounds and oxa-derivatives thereof
EP1534676B1 (en) 2002-07-17 2012-09-12 Actelion Pharmaceuticals Ltd. Piperidinetriol derivatives as inhibitors of glycosylceramide synthase
JP4585851B2 (ja) 2002-07-17 2010-11-24 アクテリオン ファーマシューティカルズ リミテッド グルコシルセラミドシンターゼの阻害剤としてのピペリジントリオール誘導体
GB0229476D0 (en) * 2002-12-17 2003-01-22 Oxford Glycosciences Uk Ltd Novel process
WO2004069190A2 (en) 2003-01-31 2004-08-19 Mount Sinai School Of Medicine Of New York University Combination therapy for treating protein deficiency disorders
GB0313677D0 (en) 2003-06-13 2003-07-16 Oxford Glycosciences Uk Ltd Novel compound
GB0313678D0 (en) 2003-06-13 2003-07-16 Oxford Glycosciences Uk Ltd Novel compounds
CN1901907A (zh) * 2003-11-12 2007-01-24 阿米库斯治疗学公司 用于治疗戈谢病的葡糖并咪唑和多羟基环己烯基胺衍生物
US20050256168A1 (en) * 2004-04-28 2005-11-17 Block Timothy M Compositions for oral administration for the treatment of interferon-responsive disorders
WO2005123055A2 (en) * 2004-06-14 2005-12-29 Musc Foundation For Research Development Methods for treating inflammatory disorders
ES2572148T3 (es) 2005-05-17 2016-05-30 Amicus Therapeutics Inc Un método para el tratamiento de la enfermedad de Pompe usando 1-desoxinojirimicina y derivados
GB0614947D0 (en) * 2006-07-27 2006-09-06 Isis Innovation Epitope reduction therapy
EP2356990A3 (en) 2006-08-02 2011-10-19 University of Oxford Liposome treatment of viral infections
WO2009118658A2 (en) * 2008-03-26 2009-10-01 University Of Oxford Endoplasmic reticulum targeting liposomes
US8703744B2 (en) * 2009-03-27 2014-04-22 The Chancellor, Masters And Scholars Of The University Of Oxford Cholesterol level lowering liposomes
EP2411526A4 (en) * 2009-03-27 2012-09-19 Zacharon Pharmaceuticals Inc MODULATORS OF GANGLIOSID BIOSYNTHESIS
RU2609210C2 (ru) 2010-12-23 2017-01-31 Алектос Терапьютикс Инк. Селективные ингибиторы гликозидазы и их применение
WO2012129651A1 (en) 2011-03-31 2012-10-04 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
US9701693B2 (en) 2011-06-27 2017-07-11 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
EP2890676B1 (en) 2012-08-31 2018-12-05 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
US9522883B2 (en) * 2012-08-31 2016-12-20 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
EP2890675A4 (en) 2012-08-31 2016-01-13 Alectos Therapeutics Inc GLYCOSIDASE INHIBITORS AND USES THEREOF
KR20150079711A (ko) 2012-10-31 2015-07-08 알렉토스 테라퓨틱스 인크. 글리코시다아제 저해제 및 이의 용도
ES2779006T3 (es) * 2013-01-09 2020-08-13 Amicus Therapeutics Inc Composiciones de DNJ parenterales estables
AU2018278247B2 (en) 2017-06-01 2022-07-28 Idorsia Pharmaceuticals Ltd Crystalline form of N-butyldeoxygalactonojirimycin
EP4034256B1 (en) 2019-09-25 2025-11-19 Assia Chemical Industries Ltd. Solid state forms of lucerastat salts and process for preparation thereof
WO2022132992A1 (en) 2020-12-16 2022-06-23 Amicus Therapeutics, Inc. Highly purified batches of pharmaceutical grade 1-deoxygalactonojirimycin compounds
US11623916B2 (en) 2020-12-16 2023-04-11 Amicus Therapeutics, Inc. Highly purified batches of pharmaceutical grade migalastat and methods of producing the same
WO2025017212A1 (en) 2023-07-20 2025-01-23 Katholieke Universiteit Leuven Udp-glucose ceramide glucosyltransferase synthase (ugcg) inhibitors in the treatment of cancer

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1555654A (en) 1977-06-25 1979-11-14 Exxon Research Engineering Co Agricultural burner apparatus
US4065562A (en) 1975-12-29 1977-12-27 Nippon Shinyaku Co., Ltd. Method and composition for reducing blood glucose levels
NO154918C (no) 1977-08-27 1987-01-14 Bayer Ag Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
GB2020278B (en) 1978-05-03 1983-02-23 Nippon Shinyaku Co Ltd Moranoline dervitives
EP0252962B1 (en) 1985-12-23 1995-08-23 Fred Hutchinson Cancer Research Center Regulating retroviral replication, infection, and pathogenesis
US4849430A (en) 1988-03-09 1989-07-18 Monsanto Company Method of inhibiting virus
US5011829A (en) * 1989-06-02 1991-04-30 G. D. Searle & Co. Pharmaceutical composition and method of inhibiting virus
US5030638A (en) 1990-02-26 1991-07-09 G. D. Searle & Co. Method of antiviral enhancement
WO1992000277A1 (en) 1990-06-29 1992-01-09 Nippon Shinyaku Co., Ltd. Piperidine derivative
US5128347A (en) * 1990-10-18 1992-07-07 Monsanto Company Glycosidase inhibiting 1,4-dideoxy-4-fluoronojirimycin

Also Published As

Publication number Publication date
US5786368A (en) 1998-07-28
JPH08510244A (ja) 1996-10-29
CA2159988A1 (en) 1994-11-24
DE69401658T2 (de) 1997-06-12
EP0698012B1 (en) 1997-01-29
JP3636363B2 (ja) 2005-04-06
ATE148456T1 (de) 1997-02-15
DE69401658D1 (de) 1997-03-13
GR3022554T3 (en) 1997-05-31
US5580884A (en) 1996-12-03
US6291657B1 (en) 2001-09-18
DK0698012T3 (enExample) 1997-02-17
EP0698012A1 (en) 1996-02-28
AU6783294A (en) 1994-12-12
WO1994026714A1 (en) 1994-11-24
ES2097653T3 (es) 1997-04-01

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CA2159988C (en) Novel deoxygalactonojirimycin derivatives
US5399567A (en) Method of treating cholera
Platt et al. N-butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N-linked oligosaccharide processing.
Butters et al. Molecular requirements of imino sugars for the selective control of N-linked glycosylation and glycosphingolipid biosynthesis
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Effective date: 20100511