CA2093078A1 - 2-substituted tertiary carbinol derivatives of 1,5-iminosugars - Google Patents

2-substituted tertiary carbinol derivatives of 1,5-iminosugars

Info

Publication number
CA2093078A1
CA2093078A1 CA002093078A CA2093078A CA2093078A1 CA 2093078 A1 CA2093078 A1 CA 2093078A1 CA 002093078 A CA002093078 A CA 002093078A CA 2093078 A CA2093078 A CA 2093078A CA 2093078 A1 CA2093078 A1 CA 2093078A1
Authority
CA
Canada
Prior art keywords
iminosugars
substituted tertiary
carbinol derivatives
tertiary carbinol
derivatives
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.)
Granted
Application number
CA002093078A
Other languages
French (fr)
Other versions
CA2093078C (en
Inventor
Ish Kumar Khanna
Richard August Mueller
Richard Mathias Weier
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
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2093078A1 publication Critical patent/CA2093078A1/en
Application granted granted Critical
Publication of CA2093078C publication Critical patent/CA2093078C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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

Abstract

Novel 2-alkyl carbinol derivatives of deoxynojirimycin (DNJ) and the chemical synthesis of these derivatives and intermediates therefor from DNJ
and their method of inhibiting lentiviruses are disclosed.
CA002093078A 1992-04-01 1993-03-31 2-substituted tertiary carbinol derivatives of 1,5-iminosugars Expired - Fee Related CA2093078C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/861,058 US5258518A (en) 1992-04-01 1992-04-01 2-substituted tertiary carbinol derivatives of deoxynojirimycin
US07/861,058 1992-04-01

Publications (2)

Publication Number Publication Date
CA2093078A1 true CA2093078A1 (en) 1993-10-02
CA2093078C CA2093078C (en) 2005-02-22

Family

ID=25334759

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002093078A Expired - Fee Related CA2093078C (en) 1992-04-01 1993-03-31 2-substituted tertiary carbinol derivatives of 1,5-iminosugars

Country Status (9)

Country Link
US (7) US5258518A (en)
EP (1) EP0566556B1 (en)
JP (1) JP3210772B2 (en)
AT (1) ATE139998T1 (en)
CA (1) CA2093078C (en)
DE (1) DE69303413T2 (en)
DK (1) DK0566556T3 (en)
ES (1) ES2090948T3 (en)
GR (1) GR3021228T3 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
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US5451679A (en) * 1994-03-08 1995-09-19 G. D. Searle & Co. 2-chloro and 2-bromo derivatives of 1,5-iminosugars
EP2295415A1 (en) * 1995-03-30 2011-03-16 OSI Pharmaceuticals, Inc. Quinazoline derivatives
US5840711A (en) * 1995-06-21 1998-11-24 University Of Kentucky Research Foundation Compositions containing lithium inorganic salts and anti-viral drugs and method of treating viral infections such as acquired immunodeficiency syndrome
US20030100532A1 (en) 1997-02-14 2003-05-29 Gary S. Jacob Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy for treating hepatitis virus infections
AU753336B2 (en) 1997-11-10 2002-10-17 G.D. Searle & Co. Use of alkylated iminosugars to treat multidrug resistance
US6689759B1 (en) 1998-02-12 2004-02-10 G. D. Searle & Co. Methods of Treating hepatitis virus infections with N-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy
ID27290A (en) 1998-02-12 2001-03-22 Searle & Co USE OF 1,5-DIDEOKSI-1,5-IMINO-D-GLUSITOL-N-SUBSTITUTED N-COMPOUND IN TREATMENT OF HEPATITIC VIRUS INFECTION
US6545021B1 (en) 1999-02-12 2003-04-08 G.D. Searle & Co. Use of substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds for treating hepatitis virus infections
CA2362785A1 (en) 1999-02-12 2001-02-08 G.D. Searle & Co. Glucamine compounds for treating hepatitis virus infections
EP1888612A1 (en) * 2005-06-08 2008-02-20 Amicus Therapeutics, Inc. Crystalline sugar compositions and method of making
BRPI0613224A2 (en) * 2005-06-08 2010-12-28 Amicus Therapeutics Inc method for stabilizing a tri-canned sugar, method for increasing reaction yield of a sugar product and stabilized tri-canned sugar composition
JP5107350B2 (en) * 2005-06-08 2012-12-26 アミカス セラピューティックス インコーポレイテッド Purification of imino and amino sugars
JP6166150B2 (en) * 2013-10-29 2017-07-19 アルプス電気株式会社 Receiver
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 (31)

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NO154918C (en) * 1977-08-27 1987-01-14 Bayer Ag ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE DERIVATIVES OF 3,4,5-TRIHYDROXYPIPERIDINE.
GB2020278B (en) * 1978-05-03 1983-02-23 Nippon Shinyaku Co Ltd Moranoline dervitives
US4182763A (en) * 1978-05-22 1980-01-08 Mead Johnson & Company Buspirone anti-anxiety method
DE2848117A1 (en) * 1978-11-06 1980-05-14 Bayer Ag DERIVATIVES OF 2-HYDROXYMETHYL-3,4,5-TRIHYDROXY-PIPERIDINE, THEIR PRODUCTION AND USE THEREFORE INFLUENCING THE CARBOHYDRATE AND FATTY METHODOLOGY
DE3007078A1 (en) * 1980-02-26 1981-09-10 Bayer Ag, 5090 Leverkusen NEW DERIVATIVES OF 3,4,5-TRIHYDROXYPIPERIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT AND IN ANIMAL FOOD
US4632992A (en) * 1981-02-09 1986-12-30 Pfizer Inc. Intermediates for preparing pirbuterol and analogs
DE3620645A1 (en) * 1985-12-20 1987-07-02 Bayer Ag 3-AMINO-4,5-DIHYDROXYPIPERIDINE, METHOD FOR THE PRODUCTION AND USE THEREOF
EP0252962B1 (en) * 1985-12-23 1995-08-23 Fred Hutchinson Cancer Research Center Regulating retroviral replication, infection, and pathogenesis
DE3611841A1 (en) * 1986-04-09 1987-10-15 Bayer Ag METHOD FOR PRODUCING 1-DESOXYNOJIRIMYCIN AND ITS N-DERIVATIVES
EP0282618A1 (en) * 1987-03-18 1988-09-21 Vereniging Het Nederlands Kanker Instituut 1-Deoxynojirimycin as an anti-HIV therapeutic
JPS6461459A (en) * 1987-08-28 1989-03-08 Nippon Shinyaku Co Ltd Moranoline derivative
US4849430A (en) * 1988-03-09 1989-07-18 Monsanto Company Method of inhibiting virus
US4999360A (en) * 1987-12-21 1991-03-12 Monsanto Company Method of inhibiting virus
US4861892A (en) * 1988-02-12 1989-08-29 G. D. Searle & Co. Method for synthesis of deoxymannojirimycin
US5003072A (en) * 1988-11-03 1991-03-26 G. D. Searle & Co. 1,5-dideoxy-1,5-imino-D-glucitol derivatives
US5144037A (en) * 1988-11-03 1992-09-01 G. D. Searle & Co. 1,5-dideoxy-1,5-imino-d-glucitol derivatives
US4957926A (en) * 1988-12-22 1990-09-18 Monsanto Company Method of treating herpesviruses
US5011829A (en) * 1989-06-02 1991-04-30 G. D. Searle & Co. Pharmaceutical composition and method of inhibiting virus
US5175168A (en) * 1989-07-27 1992-12-29 Monsanto Company Intermediates for 1,2-dideoxy-2-fluoronojirimycin
US5026713A (en) * 1989-08-29 1991-06-25 Monsanto Company 1,3-dideoxy-3-fluoronojirimycin which inhibits glycosidase activity
US5025021A (en) * 1989-07-27 1991-06-18 Monsanto Company 1,2-dideoxy-2-fluoronojirimycin as glycosidase inhibitors
ES2036512T3 (en) * 1989-07-27 1996-03-01 Monsanto Co PIPERIDINE COMPOUNDS WITH GLYCOSIDASE INHIBITING ACTIVITY.
US5130320A (en) * 1989-08-29 1992-07-14 Monsanto Company Glycosidase inhibiting 1,3-dideoxy-3-fluoronojirimycin
US5218121A (en) * 1989-08-29 1993-06-08 Monsanto Company Synthesis of 1,3-dideoxy-3-fluoronojirimycin
US5030638A (en) * 1990-02-26 1991-07-09 G. D. Searle & Co. Method of antiviral enhancement
DE4009561A1 (en) * 1990-03-24 1991-09-26 Bayer Ag New anti-retroviral desoxy:nojirimycin derivs.
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
US5128347A (en) * 1990-10-18 1992-07-07 Monsanto Company Glycosidase inhibiting 1,4-dideoxy-4-fluoronojirimycin
US5206251A (en) * 1992-04-01 1993-04-27 G. D. Searle & Co. 2- and 3- amino and azido derivatives of 1,5-iminosugars
US5331096A (en) * 1992-04-01 1994-07-19 G. D. Searle & Co. 2- and 3-sulfur derivatives of 1,5-iminosugars
US5216168A (en) * 1992-04-01 1993-06-01 G. D. Searle & Co. 2- and 3- amino and azido derivatives of 1,5-iminosugars

Also Published As

Publication number Publication date
DE69303413T2 (en) 1997-01-09
DE69303413D1 (en) 1996-08-08
US5639882A (en) 1997-06-17
US5258518A (en) 1993-11-02
JP3210772B2 (en) 2001-09-17
US5350854A (en) 1994-09-27
EP0566556B1 (en) 1996-07-03
US5523406A (en) 1996-06-04
US5530132A (en) 1996-06-25
EP0566556A1 (en) 1993-10-20
ES2090948T3 (en) 1996-10-16
ATE139998T1 (en) 1996-07-15
US5637707A (en) 1997-06-10
US5502193A (en) 1996-03-26
DK0566556T3 (en) 1996-08-19
JPH06279408A (en) 1994-10-04
CA2093078C (en) 2005-02-22
GR3021228T3 (en) 1997-01-31

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Legal Events

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EEER Examination request
MKLA Lapsed
MKLA Lapsed

Effective date: 20070402