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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Oncology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (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
GB0313679.3 2003-06-13
GB0313679A GB0313679D0 (en) 2003-06-13 2003-06-13 Novel compounds
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
US7994198B2 (en) * 2002-07-17 2011-08-09 Actelion Pharmaceuticals Ltd. Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
WO2004007453A1 (en) 2002-07-17 2004-01-22 Oxford Glycosciences (Uk) Ltd Piperidinetriol derivatives as inhibitors of glycosylceramide synthase
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
WO2005092334A2 (en) * 2004-03-25 2005-10-06 David Priestman Use of n-substituted imino sugars for appetite suppression
BRPI0517701A8 (pt) 2004-11-10 2018-01-23 Genzyme Corp métodos de tratamento de diabetes mellitus
US8716327B2 (en) 2006-05-09 2014-05-06 Genzyme Corporation Methods of treating fatty liver disease
EP2594565B1 (en) 2007-05-31 2018-10-24 Genzyme Corporation 2-acylaminopropanol-type glucosylceramide synthase inhibitors
CN102940627A (zh) 2007-10-05 2013-02-27 简詹姆公司 使用脑酰胺衍生物治疗多囊性肾疾病的方法
CA2731685A1 (en) 2008-07-28 2010-02-04 Genzyme Corporation Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease
MX2011003517A (es) 2008-10-03 2011-05-25 Genzyme Corp Inhibidores de la glucosilceramida sintasa tipo 2-acilaminopropanol.
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
PT2685986T (pt) * 2011-03-18 2020-03-05 Genzyme Corp Inibidor de glicosilceramida-sintase
JOP20130273B1 (ar) 2012-09-11 2021-08-17 Genzyme Corp مثبطات انزيم (سينثاز) غلوكوسيل سيراميد
JP6826986B2 (ja) * 2014-11-05 2021-02-10 エマージェント バイロロジー エルエルシー ウィルス性疾患の治療に有用なイミノ糖類
US20200262800A1 (en) * 2015-11-16 2020-08-20 Ptc Therapeutics, Inc. Hydrogen isotope-enriched analogues of 1,2,4-oxadiazole benzoic acid compounds, compositions and uses thereof
JP7594548B2 (ja) 2019-05-10 2024-12-04 アレクトス セラピューティックス インコーポレイテッド 非リソソームグルコシルセラミダーゼ阻害剤及びその使用
US12083115B2 (en) 2020-02-03 2024-09-10 Genzyme Corporation Methods for treating neurological symptoms associated with lysosomal storage diseases
CN115803025B (zh) 2020-05-07 2025-09-02 阿勒克图治疗公司 非溶酶体葡糖神经酰胺酶抑制剂及其用途
IL297972A (en) * 2020-05-07 2023-01-01 Alectos Therapeutics Inc 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
EP0536402A4 (en) 1990-06-29 1993-05-12 Nippon Shinyaku Company, Limited 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
US5798366A (en) 1993-05-13 1998-08-25 Monsanto Company Method for treatment of CNS-involved lysosomal storage diseases
US6291657B1 (en) 1993-05-13 2001-09-18 Monsanto Company Deoxygalactonojirimycin derivatives
EP0912179B1 (en) 1996-07-15 2006-04-12 MacroZyme DNM B.V. Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors
WO1998050359A1 (en) 1997-05-06 1998-11-12 Novo Nordisk A/S Novel heterocyclic compounds
US6426198B1 (en) 1997-07-03 2002-07-30 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Genes for Niemann-Pick type C disease
AU753336B2 (en) * 1997-11-10 2002-10-17 G.D. Searle & Co. Use of alkylated iminosugars to treat multidrug resistance
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
GB0100889D0 (en) * 2001-01-12 2001-02-21 Oxford Glycosciences Uk Ltd Compounds
GB9909064D0 (en) * 1999-04-20 1999-06-16 Oxford Glycosciences Uk Ltd Therapies
JP2003505430A (ja) 1999-07-26 2003-02-12 ジー・ディー・サール・アンド・カンパニー デオキシノジリマイシンの長鎖ｎ−アルキル誘導体およびグルコセレブロシダーゼ酵素の糖脂質異常蓄積疾患の治療用の薬剤の製造のための使用
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
WO2003075916A1 (en) * 2002-03-13 2003-09-18 Van Der Spoel Aarnoud C A non-hormonal approach to male contraception
WO2004007453A1 (en) 2002-07-17 2004-01-22 Oxford Glycosciences (Uk) Ltd Piperidinetriol derivatives as inhibitors of glycosylceramide synthase
US7994198B2 (en) 2002-07-17 2011-08-09 Actelion Pharmaceuticals Ltd. Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
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
GB0400812D0 (en) 2004-01-14 2004-02-18 Celltech R&D Ltd Novel compounds

Also Published As

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

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