CA2492404C - Piperidinetriol derivatives as inhibitors of glycosylceramide synthase - Google Patents

Piperidinetriol derivatives as inhibitors of glycosylceramide synthase Download PDF

Info

Publication number
CA2492404C
CA2492404C CA2492404A CA2492404A CA2492404C CA 2492404 C CA2492404 C CA 2492404C CA 2492404 A CA2492404 A CA 2492404A CA 2492404 A CA2492404 A CA 2492404A CA 2492404 C CA2492404 C CA 2492404C
Authority
CA
Canada
Prior art keywords
hydroxymethyl
methyl
compound
phenyl
piperidinetriol
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
CA2492404A
Other languages
English (en)
French (fr)
Other versions
CA2492404A1 (en
Inventor
Mezher Hussein Ali
Michael Glen Orchard
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.)
Idorsia Pharmaceuticals Ltd
Original Assignee
Actelion Pharmaceuticals Ltd
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 GB0216656A external-priority patent/GB0216656D0/en
Priority claimed from GB0301480A external-priority patent/GB0301480D0/en
Priority claimed from GB0313679A external-priority patent/GB0313679D0/en
Application filed by Actelion Pharmaceuticals Ltd filed Critical Actelion Pharmaceuticals Ltd
Publication of CA2492404A1 publication Critical patent/CA2492404A1/en
Application granted granted Critical
Publication of CA2492404C publication Critical patent/CA2492404C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16—Masculine contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • 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
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
    • C07D413/06—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 only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Pulmonology (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Vascular Medicine (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Oncology (AREA)
  • Reproductive Health (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2492404A 2002-07-17 2003-07-17 Piperidinetriol derivatives as inhibitors of glycosylceramide synthase Expired - Fee Related CA2492404C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GB0216656.9 2002-07-17
GB0216656A GB0216656D0 (en) 2002-07-17 2002-07-17 Novel compounds
GB0301480.0 2003-01-22
GB0301480A GB0301480D0 (en) 2003-01-22 2003-01-22 Novel compounds
GB0313679A GB0313679D0 (en) 2003-06-13 2003-06-13 Novel compounds
GB0313679.3 2003-06-13
PCT/GB2003/003099 WO2004007453A1 (en) 2002-07-17 2003-07-17 Piperidinetriol derivatives as inhibitors of glycosylceramide synthase

Publications (2)

Publication Number Publication Date
CA2492404A1 CA2492404A1 (en) 2004-01-22
CA2492404C true CA2492404C (en) 2012-02-07

Family

ID=30118831

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2492404A Expired - Fee Related CA2492404C (en) 2002-07-17 2003-07-17 Piperidinetriol derivatives as inhibitors of glycosylceramide synthase

Country Status (7)

Country Link
US (1) US7985760B2 (enExample)
EP (1) EP1534676B1 (enExample)
JP (1) JP4575156B2 (enExample)
AU (1) AU2003246942B2 (enExample)
CA (1) CA2492404C (enExample)
ES (1) ES2393331T3 (enExample)
WO (1) WO2004007453A1 (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0100889D0 (en) 2001-01-12 2001-02-21 Oxford Glycosciences Uk Ltd Compounds
WO2004007453A1 (en) 2002-07-17 2004-01-22 Oxford Glycosciences (Uk) 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
GB0313678D0 (en) * 2003-06-13 2003-07-16 Oxford Glycosciences Uk Ltd Novel compounds
GB0313677D0 (en) 2003-06-13 2003-07-16 Oxford Glycosciences Uk Ltd Novel compound
EP1528056A1 (en) * 2003-10-29 2005-05-04 Academisch Ziekenhuis bij de Universiteit van Amsterdam Deoxynojirimycin analogues and their uses as glucosylceramidase inhibitors
EP1746992A2 (en) * 2004-03-25 2007-01-31 United Therapeutics Use of n-substituted imino sugars for appetite suppression
EP1811991B1 (en) * 2004-11-10 2018-11-07 Genzyme Corporation Treatment of type 2 diabetes using inhibitors of glycosphingolipid synthesis
PT2032134E (pt) * 2006-05-09 2015-10-07 Genzyme Corp Métodos de tratamento da doença do fígado gorduroso
EP2594563B1 (en) 2007-05-31 2018-07-18 Genzyme Corporation 2-acylaminopropanol-type glucosylceramide synthase inhibitors
SG10201707161PA (en) * 2007-10-05 2017-10-30 Genzyme Corp Method of treating polycystic kidney diseases with ceramide derivatives
US8389517B2 (en) 2008-07-28 2013-03-05 Genzyme Corporation Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease
CA2738768C (en) 2008-10-03 2017-10-31 Genzyme Corporation 2-acylaminopropoanol-type glucosylceramide synthase inhibitors
WO2011085544A1 (zh) * 2010-01-13 2011-07-21 安徽辉克药业有限公司 有效清除肿瘤细胞的化合物
UA118248C2 (uk) * 2011-03-18 2018-12-26 Джензім Корпорейшн Інгібітори глюкозилцерамідсинтази
MA37975B2 (fr) 2012-09-11 2021-03-31 Genzyme Corp Inhibiteurs de synthase de glucosylcéramide
US10428022B2 (en) 2014-11-05 2019-10-01 Emergent Virology Llc Iminosugars useful for the treatment of viral diseases
EP3377476B1 (en) * 2015-11-16 2022-10-26 PTC Therapeutics, Inc. Hydrogen isotope-enriched analogues of 1,2,4-oxadiazole benzoic acid compounds, compositions and uses thereof
WO2020229968A1 (en) 2019-05-10 2020-11-19 Alectos Therapeutics Inc. Non-lysosomal glucosylceramidase inhibitors and uses thereof
US12083115B2 (en) 2020-02-03 2024-09-10 Genzyme Corporation Methods for treating neurological symptoms associated with lysosomal storage diseases
CR20220600A (es) * 2020-05-07 2023-04-11 Alectos Therapeutics Inc Inhibidores de glucosilceramidasa no lisosomal y los usos de los mismos
US20230174486A1 (en) * 2020-05-07 2023-06-08 ALECTOS THERAPEUTICS lNC. Non-lysosomal glucosylceramidase inhibitors and uses thereof
BR112023000798A2 (pt) 2020-07-24 2023-02-07 Genzyme Corp Composições farmacêuticas compreendendo venglustat

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3495570A (en) * 1967-07-03 1970-02-17 Amchem Prod Applicator for liquid chemical conversion coating material
NO154918C (no) * 1977-08-27 1987-01-14 Bayer Ag Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
DE3007078A1 (de) * 1980-02-26 1981-09-10 Bayer Ag, 5090 Leverkusen Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel sowie in der tierernaehrung
DE3024901A1 (de) 1980-07-01 1982-01-28 Bayer Ag, 5090 Leverkusen Herbizide mittel auf basis von piperidin-derivaten
DE3247615A1 (de) * 1982-12-23 1984-07-05 Hoechst Ag, 6230 Frankfurt Substituierte phenylsulfonyloxybenzimidazolcarbaminate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3737523A1 (de) * 1987-11-05 1989-05-18 Bayer Ag Verwendung von substituierten hydroxypiperidinen als antivirale mittel
US5003072A (en) * 1988-11-03 1991-03-26 G. D. Searle & Co. 1,5-dideoxy-1,5-imino-D-glucitol derivatives
JPH02306962A (ja) 1989-05-19 1990-12-20 Meiji Seika Kaisha Ltd 新規ｎ―置換―１―デオキシノジリマイシン誘導体及びそれを含有する癌細胞転移抑制剤
JPH0324057A (ja) 1989-06-22 1991-02-01 Tosoh Corp ポリヒドロキシピペリジン類及びその製造法
EP0491041A4 (en) 1989-09-07 1993-03-03 Nippon Shinyaku Company, Limited Antiviral drug
WO1992000277A1 (en) * 1990-06-29 1992-01-09 Nippon Shinyaku Co., Ltd. Piperidine derivative
US5276120A (en) * 1991-05-30 1994-01-04 The Scripps Research Institute Process for forming omega-deuxy-azasugars
US5916759A (en) 1993-05-05 1999-06-29 Boehringer Mannheim Gmbh Cholesterol oxidase from Brevibacterium sterolicum
US6291657B1 (en) 1993-05-13 2001-09-18 Monsanto Company Deoxygalactonojirimycin derivatives
US5798366A (en) * 1993-05-13 1998-08-25 Monsanto Company Method for treatment of CNS-involved lysosomal storage diseases
WO1998002161A1 (en) 1996-07-15 1998-01-22 Universiteit Van Amsterdam Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors
IL132170A0 (en) * 1997-05-06 2001-03-19 Novo Nordisk As Novel heterocyclic compounds
WO1999001555A1 (en) * 1997-07-03 1999-01-14 The United States Of America Represented By The Secretary, Department Of Health And Human Services Genes for niemann-pick type c disease
ES2216327T3 (es) 1997-11-10 2004-10-16 G.D. SEARLE & CO. Uso de iminoazucares alquilados para tratar la resistencia a multiples a farmacos.
US6610703B1 (en) 1998-12-10 2003-08-26 G.D. Searle & Co. Method for treatment of glycolipid storage diseases
WO2000056334A1 (en) 1999-03-19 2000-09-28 The Trustees Of Boston College Use of imino sugars for anti-tumor therapy
GB9909064D0 (en) 1999-04-20 1999-06-16 Oxford Glycosciences Uk Ltd Therapies
GB0100889D0 (en) * 2001-01-12 2001-02-21 Oxford Glycosciences Uk Ltd Compounds
CA2378776A1 (en) * 1999-07-26 2001-02-01 G.D. Searle & Co. Use of long-chain n-alkyl derivatives of deoxynojirimycin and a glucocerebrosidase enzyme for the manufacture of medicament for the treatment of glycolipid storage diseases
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
JP2003506406A (ja) 1999-08-10 2003-02-18 ザ・チャンセラー・マスターズ・アンド・スカラーズ・オブ・ザ・ユニバーシティ・オブ・オックスフォード 長鎖ｎ−アルキル化合物およびそのオキサ誘導体
CA2479027A1 (en) * 2002-03-13 2003-09-18 Aarnoud C. Van Der Spoel A non-hormonal approach to male contraception
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
WO2004007453A1 (en) 2002-07-17 2004-01-22 Oxford Glycosciences (Uk) Ltd Piperidinetriol derivatives as inhibitors of glycosylceramide synthase
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
GB0400812D0 (en) 2004-01-14 2004-02-18 Celltech R&D Ltd Novel compounds

Also Published As

Publication number Publication date
ES2393331T3 (es) 2012-12-20
EP1534676A1 (en) 2005-06-01
US20060058349A1 (en) 2006-03-16
JP4575156B2 (ja) 2010-11-04
US7985760B2 (en) 2011-07-26
WO2004007453A1 (en) 2004-01-22
AU2003246942B2 (en) 2009-06-25
JP2005536503A (ja) 2005-12-02
CA2492404A1 (en) 2004-01-22
AU2003246942A1 (en) 2004-02-02
EP1534676B1 (en) 2012-09-12

Similar Documents

Publication Publication Date Title
CA2492404C (en) Piperidinetriol derivatives as inhibitors of glycosylceramide synthase
US20080234324A1 (en) Piperidine Derivatives as Gcs Inhibitors
WO2002055498A1 (en) Pharmaceutically active piperidine derivatives
CA2492410C (en) Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
JP4780785B2 (ja) Ｇｃｓ阻害剤としてのピペリジン誘導体
JP4780784B2 (ja) Ｇｃｓ阻害性ピペリジン誘導体

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20190717