WO2014017915A3 - Urea and guanidinium derivatives of iminosugars - Google Patents

Urea and guanidinium derivatives of iminosugars Download PDF

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Publication number
WO2014017915A3
WO2014017915A3 PCT/NL2013/050562 NL2013050562W WO2014017915A3 WO 2014017915 A3 WO2014017915 A3 WO 2014017915A3 NL 2013050562 W NL2013050562 W NL 2013050562W WO 2014017915 A3 WO2014017915 A3 WO 2014017915A3
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WO
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Patent type
Prior art keywords
urea
containing
aryl
alkyl
iminosugars
Prior art date
Application number
PCT/NL2013/050562
Other languages
French (fr)
Other versions
WO2014017915A2 (en )
Inventor
Roelof Jan Pieters
Nathaniel Isaac MARTIN
Hilbert Marinus BRANDERHORST
Raymond KOOIJ
Original Assignee
Universiteit Utrecht Holding B.V.
Stichting Voor De Technische Wetenschappen
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

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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
    • C07D211/46Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
    • Y02P20/55Synthetic design, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention relates to novel urea and guanidinium derivatives of deoxynojirimycin and related iminosugars, wherein the ring nitrogen in the iminosugars is derivatised, methods for the preparation urea and guanidinium derivatives of deoxynojirimycin, (protected) intermediates and the use of the urea and guanidinium derivatives of deoxynojirimycin in the modification of the activity of glycosidases and their use as a pharmaceutical. Where in is a 5, 6, 7 or 8-membered (saturated) nitrogen-containing cyclic compound; wherein X is O or NR7; wherein R1 is H or a straight or branched alkyl, cycloalkyl, alkenyl, alkynyl, alkoxyalkyl or aminoalkyl containing 1 -20 carbon atoms, an aryl, alkylaryl, heteroaryl, heteroalkyl, alkoxy(het)aryl containing 5-12 ring atoms, wherein R1 is optionally substituted with one o more -OH, -COOH, -CI, -F, -CF3, -OCF3, -O-C(=O)N-(alkyl)2; wherein R2 is H or a straight or branched alkyl, cycloalkyl, alkenyl, alkynyl, alkoxyalkyl or aminoalkyl containing 1 -12 carbon atoms, an aryl, alkylaryl, heteroaryl, heteroalkyl, alkoxy(het)aryl containing 5-12 ring atoms, wherein R1 is optionally substituted with one o more -OH, -COOH, -CI, -F, -CF3, -OCF3, -O-C(=O)N-(alkyl)2; wherein R3, R4, R5, R6 are independently H or a hydroxyl protecting group, wherein R7 is H, C1-C6 alkyl;
PCT/NL2013/050562 2012-07-27 2013-07-26 Urea and guanidinium derivatives of iminosugars WO2014017915A3 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
NL2009247 2012-07-27
NL2009246 2012-07-27
NL2009247 2012-07-27
NL2009246 2012-07-27

Publications (2)

Publication Number Publication Date
WO2014017915A2 true WO2014017915A2 (en) 2014-01-30
WO2014017915A3 true true WO2014017915A3 (en) 2014-06-12

Family

ID=48953425

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2013/050562 WO2014017915A3 (en) 2012-07-27 2013-07-26 Urea and guanidinium derivatives of iminosugars

Country Status (1)

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WO (1) WO2014017915A3 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015039010A3 (en) 2013-09-16 2015-05-07 Unither Virology, Llc Deoxynojirimycin derivatives and methods of their using

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60224675A (en) * 1984-04-24 1985-11-09 Meiji Seika Kaisha Ltd Novel 1-deoxynojirimycin derivative and hypolipemic containing the same
WO1998002161A1 (en) * 1996-07-15 1998-01-22 Universiteit Van Amsterdam Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors
WO2000033843A1 (en) * 1998-12-10 2000-06-15 G.D. Searle & Co. Use of long-chain n-alkyl derivatives of deoxynojirimycin for the manufacture of a medicament for the treatment of glycolipid storage diseases

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3611841A1 (en) 1986-04-09 1987-10-15 Bayer Ag A process for the preparation of 1-deoxynojirimycin and its N-derivatives
EP0536402A4 (en) 1990-06-29 1993-05-12 Nippon Shinyaku Company, Limited Piperidine derivative
US5273981A (en) 1990-10-18 1993-12-28 Monsanto Company Intramolecular carbamate derivative of 2,3-Di-O-blocked-1,4-dideoxy-4-fluoro-nojirimycins
CA2492410C (en) 2002-07-17 2011-09-13 Oxford Glycosciences (Uk) Ltd Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase
KR20080025373A (en) 2005-05-17 2008-03-20 아미쿠스 세라퓨틱스, 인코포레이티드 A method for the treatment of pompe disease using 1-deoxynojirimycin and derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60224675A (en) * 1984-04-24 1985-11-09 Meiji Seika Kaisha Ltd Novel 1-deoxynojirimycin derivative and hypolipemic containing the same
WO1998002161A1 (en) * 1996-07-15 1998-01-22 Universiteit Van Amsterdam Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors
WO2000033843A1 (en) * 1998-12-10 2000-06-15 G.D. Searle & Co. Use of long-chain n-alkyl derivatives of deoxynojirimycin for the manufacture of a medicament for the treatment of glycolipid storage diseases

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BINI D. ET AL: "Synthesis and biological evaluation of nojirimycin and pyrrolidine based trehalase inhibitors", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 8, 5 April 2012 (2012-04-05), pages 514 - 521, XP002694281 *
MARTIN N ET AL: "Ng-Hydroxguanidines from primary amines", ORGANIC LETTERS, vol. 8, no. 18, 29 July 2006 (2006-07-29), pages 4035 - 4038, XP002694282 *

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WO2014017915A2 (en) 2014-01-30 application

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