WO2007144503A3 - Novel process for preparing nitrones and n-hydroxylamines comprising at least one hydroxyl group, and products thus obtained - Google Patents

Novel process for preparing nitrones and n-hydroxylamines comprising at least one hydroxyl group, and products thus obtained Download PDF

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Publication number
WO2007144503A3
WO2007144503A3 PCT/FR2007/000973 FR2007000973W WO2007144503A3 WO 2007144503 A3 WO2007144503 A3 WO 2007144503A3 FR 2007000973 W FR2007000973 W FR 2007000973W WO 2007144503 A3 WO2007144503 A3 WO 2007144503A3
Authority
WO
WIPO (PCT)
Prior art keywords
functional group
hydroxylamines
products
hydroxyl group
novel process
Prior art date
Application number
PCT/FR2007/000973
Other languages
French (fr)
Other versions
WO2007144503A2 (en
Inventor
Sandrine Py
Stephanie Devergnes
Yannick Vallee
Original Assignee
Univ Joseph Fourier
Ct Nat Da La Rech Scient
Sandrine Py
Stephanie Devergnes
Yannick Vallee
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 Univ Joseph Fourier, Ct Nat Da La Rech Scient, Sandrine Py, Stephanie Devergnes, Yannick Vallee filed Critical Univ Joseph Fourier
Publication of WO2007144503A2 publication Critical patent/WO2007144503A2/en
Publication of WO2007144503A3 publication Critical patent/WO2007144503A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic 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
    • C07D207/18—Heterocyclic 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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic 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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to the use of a Lewis acid, in particular chosen from: - boron trihalides (BI3, BBr3, BCl3, BF3), - complexes of the abovementioned boron trihalides with Lewis bases such as ethers, thioethers, phosphines or amines, or - trialkylsilane halides (TMSI, TMSBr), for converting one or more alkoxyl groups to one or more hydroxyl groups, wherein said alkoxyl groups are present on cyclic or noncyclic compounds bearing a nitrone or N-hydroxylamine nitrogenous functional group, it being possible for said nitrogenous functional group to be integrated into a ring, without affecting the nitrogenous functional group.
PCT/FR2007/000973 2006-06-13 2007-06-13 Novel process for preparing nitrones and n-hydroxylamines comprising at least one hydroxyl group, and products thus obtained WO2007144503A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0605244A FR2902097A1 (en) 2006-06-13 2006-06-13 NOVEL PROCESS FOR THE PREPARATION OF NITRONES AND N-HYDROXYLAMINES COMPRISING AT LEAST ONE HYDROXYL GROUP, AND PRODUCTS SUCH AS OBTAINED
FR06/05244 2006-06-13

Publications (2)

Publication Number Publication Date
WO2007144503A2 WO2007144503A2 (en) 2007-12-21
WO2007144503A3 true WO2007144503A3 (en) 2008-05-02

Family

ID=37733729

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2007/000973 WO2007144503A2 (en) 2006-06-13 2007-06-13 Novel process for preparing nitrones and n-hydroxylamines comprising at least one hydroxyl group, and products thus obtained

Country Status (2)

Country Link
FR (1) FR2902097A1 (en)
WO (1) WO2007144503A2 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992022290A1 (en) * 1991-06-18 1992-12-23 Oklahoma Medical Research Foundation Use of spin trapping for the treatment of diseases associated with oxidation of lipids and proteins
US20040147591A1 (en) * 2001-06-08 2004-07-29 Mitsubishi Chemical Corporation Azasugar compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992022290A1 (en) * 1991-06-18 1992-12-23 Oklahoma Medical Research Foundation Use of spin trapping for the treatment of diseases associated with oxidation of lipids and proteins
US20040147591A1 (en) * 2001-06-08 2004-07-29 Mitsubishi Chemical Corporation Azasugar compound

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
ANDREA GOTI ET AL.: "Iterative Organometallic Addition to chiral Hydroxylated Cyclic Nitrones: Highly Stereoselective Syntheses of a,a'- and a,a-Substituted Hydroxypyrrolidines", ORGANIC LETTERS, vol. 5, no. 22, 10 September 2003 (2003-09-10), USAMERICAN CHEMICAL SOCIETY, pages 4235 - 4238, XP002425699 *
ASHOORZADEH A ET AL: "A CONVERGENT ENANTIOSELECTIVE SYNTHESIS OF THE ANTI-MALARIAL AGENT (+)-FEBRIFUGINE", SYNLETT, THIEME INTERNATIONAL, STUTTGART, DE, no. 2, 1 February 2005 (2005-02-01), pages 346 - 348, XP008070028, ISSN: 0936-5214 *
CICCHI S ET AL: "Manganese dioxide oxidation of hydroxylamines to nitrones", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 42, no. 37, 10 September 2001 (2001-09-10), pages 6503 - 6505, XP004299716, ISSN: 0040-4039 *
CICCHI S ET AL: "ONE-POT SYNTHESIS OF CYCLIC NITRONES AND THEIR CONVERSION TO PYRROLIZIDINES: 7A-EPI-CROTANECINE INHIBITS ALPHA-MANNOSIDASES", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 71, no. 4, 2 January 2006 (2006-01-02), pages 1614 - 1618, XP002425698, ISSN: 0022-3263 *
DEHNEL A ET AL: "DESIGNER SPIN TRAPS WITH A CYCLIC NITRONE STRUCTURE", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 53, 1988, pages 1566 - 1567, XP002425703, ISSN: 0022-3263 *
FRANCA M. CORDERO ET AL.: "Stereoselective Approach to Hydroxyindolizidines: Protection/Deprotection of nitrone Functionality via Cycloaddition/Retrocycloaddition", ORGANIC LETTERS, vol. 2, no. 16, 2000, USAMERICAN CHEMICAL SOCIETY, pages 2475 - 2477, XP002425694 *
J. GOLIK ET AL.: "Stereochemical Studies on Esperamicins: Determination of the absolute Configuration of Hydroxyamino Sugar Fragment", TETRAHEDRON LETTERS, vol. 32, no. 16, 1991, NLELSEVIER, AMSTERDAM, pages 1851 - 1854, XP002425697 *
KAWAHARA S-I ET AL: "1:1 and 1:2 Complexes of Bu4NF and BF3@?Et2O: Unique Properties as Reagents for Cleavage of Silyl Ethers", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 37, no. 4, 22 January 1996 (1996-01-22), pages 509 - 512, XP004030407, ISSN: 0040-4039 *
KOUMBIS ET AL: "1,3-DIPOLAR CYCLOADDITIONS IN THE SYNTHESIS OF CARBOHYDRATE MIMICS.PART 2: NITRONES AND OXIMES", CURRENT ORGANIC CHEMISTRY, HILVERSUM, NL, vol. 7, no. 6, 2003, pages 585 - 628, XP009079878, ISSN: 1385-2728 *
MARCO LOMBARDO ET AL: "Entropy controlled selectivity in the vinylation of a cyclic Chiral Nitrone. An efficient Route to Enantioure Polyhadroxylated Pyrrolidines", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 66, no. 4, 27 January 2001 (2001-01-27), pages 1264 - 1268, XP002425696, ISSN: 0022-3263 *
OSAMU TAMURA ET AL: "TBAT Mediated Nitrone Formation of omega-Mesyloxy-O-tert-butyldipheny lsilyloximes: Facile Synthesis of Cyclic Nitrones from Hemiacetals", SYNLETT, THIEME INTERNATIONAL, STUTTGART, DE, no. 8, 30 July 2002 (2002-07-30), pages 1344 - 1345, XP002425695, ISSN: 0936-5214 *
PHILIPPE COMPAIN ET AL: "Carbohydrate Mimetics-based Glycosyltransferase Inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 9, 2001, pages 3077 - 3092, XP002425702, ISSN: 0968-0896 *
SHUJI AKAI ET AL: "Lipase -catalysed domino kinetic resolution of a-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (-)rosmarinecine", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, 2005, pages 2369 - 2371, XP002425701, ISSN: 1359-7345 *
STÉPHANIE DESVERGNES ET AL.: "Total synthesis of (+) Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung", JOURNAL OF ORGANIC CHEMISTRY., vol. 70, no. 4, 19 January 2005 (2005-01-19), USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., pages 1459 - 1462, XP002425700 *
STOLZE ET AL: "Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 14, no. 10, 15 May 2006 (2006-05-15), pages 3368 - 3376, XP005364987, ISSN: 0968-0896 *

Also Published As

Publication number Publication date
WO2007144503A2 (en) 2007-12-21
FR2902097A1 (en) 2007-12-14

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