CA2652958C - Deoxynojirimycin and d-arabinitol analogs and methods of using - Google Patents

Deoxynojirimycin and d-arabinitol analogs and methods of using Download PDF

Info

Publication number
CA2652958C
CA2652958C CA2652958A CA2652958A CA2652958C CA 2652958 C CA2652958 C CA 2652958C CA 2652958 A CA2652958 A CA 2652958A CA 2652958 A CA2652958 A CA 2652958A CA 2652958 C CA2652958 C CA 2652958C
Authority
CA
Canada
Prior art keywords
substituted
groups
compound
unsubstituted
formula
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
CA2652958A
Other languages
English (en)
French (fr)
Other versions
CA2652958A1 (en
Inventor
Terry D. Butters
Raymond A. Dwek
George W. J. Fleet
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.)
University of Oxford
Original Assignee
United Therapeutics Corp
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 United Therapeutics Corp filed Critical United Therapeutics Corp
Publication of CA2652958A1 publication Critical patent/CA2652958A1/en
Application granted granted Critical
Publication of CA2652958C publication Critical patent/CA2652958C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/36Heterocyclic 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
    • C07D211/40Oxygen atoms
    • C07D211/44Oxygen atoms attached in position 4
    • C07D211/48Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/12Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/36Heterocyclic 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
    • C07D211/40Oxygen atoms
    • C07D211/44Oxygen atoms attached in position 4
    • C07D211/46Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2652958A 2006-05-24 2007-05-22 Deoxynojirimycin and d-arabinitol analogs and methods of using Expired - Fee Related CA2652958C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US80277606P 2006-05-24 2006-05-24
US60/802,776 2006-05-24
PCT/US2007/069448 WO2007140184A2 (en) 2006-05-24 2007-05-22 Deoxynojirimycin and d-arabinitol analogs and methods of using

Publications (2)

Publication Number Publication Date
CA2652958A1 CA2652958A1 (en) 2007-12-06
CA2652958C true CA2652958C (en) 2015-11-17

Family

ID=38779322

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2652958A Expired - Fee Related CA2652958C (en) 2006-05-24 2007-05-22 Deoxynojirimycin and d-arabinitol analogs and methods of using

Country Status (8)

Country Link
US (1) US8975280B2 (enExample)
EP (1) EP2023927B1 (enExample)
JP (2) JP5241709B2 (enExample)
CN (2) CN104876855A (enExample)
CA (1) CA2652958C (enExample)
ES (1) ES2537572T3 (enExample)
HK (1) HK1214261A1 (enExample)
WO (1) WO2007140184A2 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080138351A1 (en) * 2006-08-02 2008-06-12 United Therapeutics Corporation Liposome treatment of viral infections
US20090252785A1 (en) * 2008-03-26 2009-10-08 University Of Oxford Endoplasmic reticulum targeting liposomes
JP5600329B2 (ja) * 2009-02-23 2014-10-01 ユナイテッド セラピューティクス コーポレーション イミノ糖およびウイルス性疾患を治療する方法
KR101787434B1 (ko) 2009-02-24 2017-11-15 유나이티드 세러퓨틱스 코오포레이션 이미노슈가 및 아레나바이러스성 감염을 치료하는 방법
CN102427804A (zh) * 2009-03-27 2012-04-25 牛津大学之校长及学者 降低胆固醇水平的脂质体
WO2010111711A2 (en) * 2009-03-27 2010-09-30 Zacharon Pharmaceuticals, Inc. Ganglioside biosynthesis modulators
JP5634510B2 (ja) * 2009-06-12 2014-12-03 ユナイテッド セラピューティクス コーポレイション イミノ糖ならびにブニヤウイルスおよびトガウイルス疾患を治療する方法
KR101497194B1 (ko) * 2009-09-04 2015-02-27 유나이티드 세러퓨틱스 코오포레이션 오르토믹소바이러스 감염의 치료 방법
JP5752689B2 (ja) * 2009-09-04 2015-07-22 ユナイテッド セラピューティクス コーポレイション フィロウイルス疾患を治療するイミノ糖および方法
KR101459530B1 (ko) * 2009-09-04 2014-11-07 유나이티드 세러퓨틱스 코오포레이션 폭스바이러스 감염의 치료 방법
CN104703597A (zh) 2012-06-06 2015-06-10 尤尼特尔滤过性微生物学有限责任公司 新型亚氨基糖及它们的应用
CN105246478A (zh) 2013-03-15 2016-01-13 优尼特尔病毒学公司 抗菌化合物
HK1221871A1 (zh) * 2013-05-02 2017-06-16 The Chancellor, Masters And Scholars Of The University Of Oxford 使用亚氨基糖进行的糖脂抑制
MX2016003323A (es) 2013-09-16 2016-08-12 Emergent Virology Llc Derivados de dosoxinojirimicina y sus metodos de uso.
CA2966893C (en) 2014-11-05 2023-10-24 Emergent Virology Llc Iminosugars
EP3318277A1 (en) 2016-11-04 2018-05-09 Institut du Cerveau et de la Moelle Epiniere-ICM Inhibitors of glucosylceramide synthase for the treatment of motor neuron diseases

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO154918C (no) 1977-08-27 1987-01-14 Bayer Ag Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
JPS54106477A (en) 1978-02-03 1979-08-21 Nippon Shinyaku Co Ltd Moranoline derivative
JPS5943947B2 (ja) * 1978-05-03 1984-10-25 日本新薬株式会社 N−置換モラノリン誘導体
JPS5943949B2 (ja) 1978-09-29 1984-10-25 日本新薬株式会社 モラノリンのn−置換誘導体
JPS5943948B2 (ja) * 1978-07-06 1984-10-25 日本新薬株式会社 置換モラノリン誘導体
GB2020278B (en) 1978-05-03 1983-02-23 Nippon Shinyaku Co Ltd Moranoline dervitives
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
JPS62155291A (ja) 1985-12-20 1987-07-10 バイエル・アクチエンゲゼルシヤフト 3−アミノ−4,5−ジヒドロキシピペリジン類、それらの製造方法及びそれらの使用
DE3620645A1 (de) 1985-12-20 1987-07-02 Bayer Ag 3-amino-4,5-dihydroxypiperidine, verfahren zu ihrer herstellung und ihre verwendung
DE3737523A1 (de) 1987-11-05 1989-05-18 Bayer Ag Verwendung von substituierten hydroxypiperidinen als antivirale mittel
JPH0643306B2 (ja) * 1988-02-12 1994-06-08 明治製菓株式会社 癌細胞転移抑制剤
US4985445A (en) 1988-02-12 1991-01-15 Meiji Seika Kaisha, Ltd. Cancer cell metastasis inhibitors and novel compounds
EP0350012A3 (en) 1988-07-08 1990-09-05 Meiji Seika Kaisha Ltd. Antiviral composition
EP0367747B1 (en) * 1988-11-03 1996-03-13 G.D. Searle & Co. Dideoxy-L-arabinitol derivatives as antiviral compounds
JPH0675510B2 (ja) 1989-02-13 1994-09-28 日本新薬株式会社 モラノリン誘導体の製法
US5256788A (en) 1989-02-13 1993-10-26 Nippon Shinyaku Co. Ltd. Moranoline derivatives and their production and the use of moranoline and its derivatives as a stabilizing agent for enzymes
US5051401A (en) * 1989-04-07 1991-09-24 University Of South Alabama Inhibition of mineral deposition by phosphorylated and related polyanionic peptides
DE4009561A1 (de) 1990-03-24 1991-09-26 Bayer Ag Neue desoxynojirimycinderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
CA2086413A1 (en) 1990-06-29 1991-12-30 Yohji Ezure Piperidine derivatives
US5290948A (en) 1990-09-17 1994-03-01 Mcneilab, Inc. Process for producing polyhydroxylated piperidines and pyrrolidines and compounds thereof
DE69421828T2 (de) 1994-01-13 2000-04-20 G.D. Searle & Co. Verwendung von 1,5-dideoxy-1,5-imino-d-glucitol n-alkylderivaten zur behandlung von hepatitis b infektionen
WO1995022975A1 (en) 1994-02-25 1995-08-31 G.D. Searle & Co. Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus
DK1030839T3 (da) 1997-11-10 2004-05-03 Searle & Co Anvendelse af alkylerede iminosukkere til behandling af multidrugresistens
US6809083B1 (en) * 1998-02-12 2004-10-26 Richard A. Mueller Use of N-substituted-1, 5-dideoxy-1, 5-imino-D-glucitol compounds for treating hepatitis virus infections
GB0100889D0 (en) * 2001-01-12 2001-02-21 Oxford Glycosciences Uk Ltd Compounds
EP1261339A1 (en) 2000-02-14 2002-12-04 Pharmacia Corporation Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds for treating hepatitis virus infections
ES2271548T3 (es) * 2002-03-13 2007-04-16 Unither Pharmaceuticals, Inc. Enfoque no hormonal de anticoncepcion masculina.
AU2003248960B2 (en) * 2002-07-17 2009-06-25 Idorsia Pharmaceuticals Ltd Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
AU2006247065B8 (en) 2005-05-17 2012-07-12 Amicus Therapeutics, Inc. A method for the treatment of Pompe disease using 1-deoxynojirimycin derivatives

Also Published As

Publication number Publication date
WO2007140184A2 (en) 2007-12-06
WO2007140184A3 (en) 2008-11-27
EP2023927A4 (en) 2013-04-10
US8975280B2 (en) 2015-03-10
US20070275998A1 (en) 2007-11-29
CN104876855A (zh) 2015-09-02
HK1214261A1 (zh) 2016-07-22
EP2023927B1 (en) 2015-02-25
ES2537572T3 (es) 2015-06-09
JP5241709B2 (ja) 2013-07-17
EP2023927A2 (en) 2009-02-18
CA2652958A1 (en) 2007-12-06
JP2013129662A (ja) 2013-07-04
CN101489554A (zh) 2009-07-22
JP2009538336A (ja) 2009-11-05

Similar Documents

Publication Publication Date Title
EP2023927B1 (en) Deoxynojirimycin and d-arabinitol analogs and methods of using
RU2556216C2 (ru) Производное индола и его фармацевтическое применение
WO2010049678A2 (en) Treatment of energy utilization diseases
NO322562B1 (no) Mutilinderivater, deres anvendelse for fremstilling av farmasoytiske midler og de derved oppnadde farmasoytiske midlene samt deres anvendelse for fremstilling av veterinaermedisinske sammensetninger.
EP0749423B1 (en) Piperidines and pyrrolidines
JPS6058751B2 (ja) プロリン関連化合物ならびにその製法
WO2010029313A1 (en) Antiinfective compounds
US6020344A (en) Enzyme inhibitors and methods of use
US4999360A (en) Method of inhibiting virus
DE60015539T2 (de) Substituierte pyrrolidine als inhibitoren der zelladhäsion
Cheng et al. Bioevaluation of sixteen ADMDP stereoisomers toward alpha-galactosidase A: Development of a new pharmacological chaperone for the treatment of Fabry disease and potential enhancement of enzyme replacement therapy efficiency
US20050049312A1 (en) Novel adamantane derivatives with neuroprotective, antidepressant and anti-ischaemic activities,and process for preparing them
SK11372001A3 (sk) Piperidínové a piperazínové deriváty ako inhibítory vzniku a'beta' fibríl
Liang et al. Design, synthesis, biologically evaluation and molecular docking of C-glycosidic oximino carbamates as novel OfHex1 inhibitors
Steiner et al. 1-Deoxygalactonojirimycin-lysine hybrids as potent D-galactosidase inhibitors
EP4603497A1 (en) Crystal form of cyano-substituted polypeptide compound and preparation method therefor
Ashmus et al. Rational design of cell active C2-modified DGJ analogues for the inhibition of human α-galactosidase A (GALA)
Iftikhar et al. An Overview of Debenzylation Methods to Obtain 1-Deoxynojirimycin (DNJ)
US20140296288A1 (en) Imino-sugar c-glycosides, preparation and use thereof
Fröhlich et al. 1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
Tanabe et al. Syntheses and evaluation as glycosidase inhibitor of 1, 5-dideoxy-1, 5-imino-d-glucitol analogs of salacinol, a potent α-glucosidase inhibitor isolated from Ayurvedic medicine, Salacia reticulata
EP3009444B1 (en) Alpha-oxoacyl amino-caprolactam derivative
NO145619B (no) Analogifremgangsmaate til fremstilling av terapeutisk aktive 1,3-dihydrospiro (isobenzofuran-1,4`-piperidiner)
CZ335095A3 (en) N-substituted azaheterocyclic carboxylic acids and esters thereof
EP0707568A1 (en) N-substituted azaheterocyclic carboxylic acids and esters thereof

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20190522