[go: up one dir, main page]

WO2010007363A3 - Preparation of fluorine-labelled compounds - Google Patents

Preparation of fluorine-labelled compounds Download PDF

Info

Publication number
WO2010007363A3
WO2010007363A3 PCT/GB2009/001742 GB2009001742W WO2010007363A3 WO 2010007363 A3 WO2010007363 A3 WO 2010007363A3 GB 2009001742 W GB2009001742 W GB 2009001742W WO 2010007363 A3 WO2010007363 A3 WO 2010007363A3
Authority
WO
WIPO (PCT)
Prior art keywords
alk
arylene
fluorine
formula
compound
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.)
Ceased
Application number
PCT/GB2009/001742
Other languages
French (fr)
Other versions
WO2010007363A2 (en
Inventor
Veronique Gouverneur
Romain Bejot
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.)
Oxford University Innovation Ltd
Original Assignee
Oxford University Innovation 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
Application filed by Oxford University Innovation Ltd filed Critical Oxford University Innovation Ltd
Publication of WO2010007363A2 publication Critical patent/WO2010007363A2/en
Publication of WO2010007363A3 publication Critical patent/WO2010007363A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a process for producing a fluorine-labelled compound, the process comprising: (a) treating a compound of formula (I) wherein R1, R2 and the C(H) group to which R1 and R2 are bonded together form a moiety to be labelled with fluorine; and the fluorous tag is a group of formula (II) wherein Rf is a straight-chained or branched C4-I2 perfluoroalkyl group; and L is a single bond, -alk-, -arylene-, -alk-arylene-, alk-X-, -arylene-X-, -alk-arylene-X, -alk- X-arylene-, -alk-X-arylene-X-, -arylene-alk-, -arylene-X-alk-, -arylene-alk-X- or - arylene-X-alk-X-, wherein X is N(R"), O, S, C(O) or C(O)N(R") and wherein alk is unsubstituted or substituted C1-10 alkylene which is optionally interrupted by N(R"), O, S, C(O), C(O)N(R") or arylene, wherein R" is C1-6 alkyl or aryl; with [nF], wherein nF is 18F or 19F, thereby fluorinating and detagging the compound of formula (I) to produce a fluorine-labelled compound of formula (III) The invention further relates to compounds of formula (I), a process for producing such compounds, and a combination product which comprises the two reactants used in that process.
PCT/GB2009/001742 2008-07-15 2009-07-14 Preparation of fluorine-labelled compounds Ceased WO2010007363A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0812923.1A GB0812923D0 (en) 2008-07-15 2008-07-15 Preparation of flourine-labelled compounds
GB0812923.1 2008-07-15

Publications (2)

Publication Number Publication Date
WO2010007363A2 WO2010007363A2 (en) 2010-01-21
WO2010007363A3 true WO2010007363A3 (en) 2010-07-01

Family

ID=39722308

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2009/001742 Ceased WO2010007363A2 (en) 2008-07-15 2009-07-14 Preparation of fluorine-labelled compounds

Country Status (2)

Country Link
GB (1) GB0812923D0 (en)
WO (1) WO2010007363A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2957345B1 (en) * 2010-03-09 2012-04-20 Polyintell PROCESS FOR PREPARING A RADIOTRICATOR
KR101195898B1 (en) 2011-01-19 2012-10-30 서강대학교산학협력단 Heterogeneous preparation of [18f]fluorinated organic compounds using base in solid state
WO2012157900A2 (en) * 2011-05-13 2012-11-22 서강대학교산학협력단 18f-labeled precursor of pet radioactive medical supplies, and preparation method thereof
CN104109111B (en) * 2013-04-22 2019-02-12 江苏豪森药业集团有限公司 Preparation method of belgliptin toxilate and intermediate thereof
CN108276469A (en) * 2017-01-06 2018-07-13 复旦大学 A method of enrichment 4- Hydroxynonenals HNE modifies peptide fragment
CN109467523A (en) * 2018-12-17 2019-03-15 苏州华道生物药业股份有限公司 A kind of green synthesis method of the third sulfonic acid chloride of 3- chlorine
CN113354593B (en) * 2021-06-28 2022-11-18 苏州大学 Fluorine-containing graft copolymer and its preparation method and application

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002090298A2 (en) * 2001-05-04 2002-11-14 Forschungszentrum Jülich GmbH Method for the synthesis of 18f marked compounds which are low in carriers
WO2006065038A1 (en) * 2004-12-15 2006-06-22 Futurechem Co., Ltd. Method for preparation of organofluoro compounds in alcohol solvents
EP2017258A1 (en) * 2006-05-11 2009-01-21 Nihon Medi-Physics Co., Ltd. Process for production of radioactive fluorine-labeled organic compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002090298A2 (en) * 2001-05-04 2002-11-14 Forschungszentrum Jülich GmbH Method for the synthesis of 18f marked compounds which are low in carriers
WO2006065038A1 (en) * 2004-12-15 2006-06-22 Futurechem Co., Ltd. Method for preparation of organofluoro compounds in alcohol solvents
EP2017258A1 (en) * 2006-05-11 2009-01-21 Nihon Medi-Physics Co., Ltd. Process for production of radioactive fluorine-labeled organic compound

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
ANDREA SCOZZAFAVA ET AL: "Carbonic anhydrase inhibitors: perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure-lowering agents with prolonged duration of action", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 43, no. 23, 16 November 2000 (2000-11-16), pages 4542 - 4551, XP002558925, ISSN: 0022-2623, [retrieved on 20001028] *
BENNUA-SKALMOWSKI B ET AL: "A Facile Conversion of Primary or Secondary Alcohols with n-Perfluorobutane-sulfonyl Fluoride/1,8-Diazabicyclo[5.4.0]undec-7-ene into their Corresponding Fluorides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 36, no. 15, 10 April 1995 (1995-04-10), pages 2611 - 2614, XP004028262, ISSN: 0040-4039 *
E. BRIARD ET AL.: "Synthesis and Evaluation of a New 18F-Labeled Ligand for PET Imaging of Brain Peripheral Benzodiazepine Receptors", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 48, no. S1, June 2005 (2005-06-01), pages S4, XP002559052 *
GRIERSON J R ET AL: "A RADIOSYNTHESIS OF FLUORINE-18 FLUOROMISONIDAZOLE", JOURNAL OF NUCLEAR MEDICINE, SOCIETY OF NUCLEAR MEDICINE, RESTON, VA, US, vol. 30, no. 3, 1 March 1989 (1989-03-01), pages 343 - 350, XP000033832, ISSN: 0161-5505 *
LISHENG CAI, SHUIYU LU, VICTOR W. PIKE: "Chemistry with [18F]Fluoride Ion", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2008, no. 17, June 2008 (2008-06-01), pages 2853 - 2873, XP002559051 *
LUTZ F TIETZE ET AL: "Enantio- and Diastereoselective synthesis of duocarmycine-based prodrugs for a selective treatment of cancer by epoxide opening", CHEMISTRY - A EUROPEAN JOURNAL, WILEY - V C H VERLAG GMBH & CO. KGAA, WEINHEIM, DE, vol. 14, no. 3, 18 January 2008 (2008-01-18), pages 895 - 901, XP002558924, ISSN: 0947-6539, [retrieved on 20071121] *
RALF SCHIRRMACHER, CARMEN WÄNGLER AND ESTHER SCHIRRMACHER: "Recent Developments and Trends in 18F-Radiochemistry: Syntheses and Applications", MINI-REVIEWS IN ORGANIC CHEMISTRY, vol. 4, no. 4, November 2007 (2007-11-01), pages 317 - 329, XP002559050 *
RICHARD C. D. BROWN ET AL.: "A Solid-Phase Route to 18F-Labeled Tracers, Exemplified by the Synthesis of [18F]2-Fluoro-2-deoxy-D-glucose", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 46, no. 6, 29 January 2007 (2007-01-29), pages 941 - 944, XP002559048 *
SANDRINE PENSEC, FRANÇOIS-GENÈS TOURNILHAC, PIERRE BASSOUL, AND CLAIRE DURLIAT: "Synthesis and Structural Studies of Polyphilic Mesogens with Central or Terminal Perfluoroalkyl Chains", THE JOURNAL OF PHYSICAL CHEMISTRY B, vol. 102, no. 1, 1 January 1998 (1998-01-01), pages 52 - 60, XP002575653 *
SOPHIE BOLDON, JANE E. MOORE AND VÉRONIQUE GOUVERNEUR: "Fluorous Synthesis of Allylic Fuorides:C-F Bond Formation as the Detagging Process", CHEMICAL COMMUNICATIONS, no. 31, 4 June 2008 (2008-06-04), pages 3622 - 3624, XP002559049 *
TEWSON T J: "Synthesis of [<18>F]Fluoroetanidazole: A Potential New Tracer for Imaging Hypoxia", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY, US, vol. 24, no. 8, 1 November 1997 (1997-11-01), pages 755 - 760, XP004097016, ISSN: 0969-8051 *
THOMAS NETSCHER ET AL: "Towards highly activating leaving groups: studies on the preparation of some halogenated alkyl sulfonates", MOLECULES, MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL, BASEL, CH, vol. 7, no. 8, 1 January 2002 (2002-01-01), pages 601 - 617, XP002558926, ISSN: 1420-3049, [retrieved on 20020831] *
VUONG ET AL: "An automated one-step one-pot [<18>F]FCWAY synthesis: development and minimization of chemical impurities", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY, US, vol. 34, no. 4, 1 May 2007 (2007-05-01), pages 433 - 438, XP022097731, ISSN: 0969-8051 *
WOLFGANG KLOTZ; RICHARD R. SCHMIDT: "Anomeric O-Alkylation of O-Acetyl-Protected Sugars", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 13, no. 8, December 1994 (1994-12-01), pages 1093 - 1101, XP008120984 *
YIN J ET AL: "Direct and Convenient Conversion of Alcohols to Fluorides", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 6, no. 9, 29 April 2004 (2004-04-29), pages 1465 - 1468, XP002993304, ISSN: 1523-7060 *

Also Published As

Publication number Publication date
WO2010007363A2 (en) 2010-01-21
GB0812923D0 (en) 2008-08-20

Similar Documents

Publication Publication Date Title
WO2010007363A3 (en) Preparation of fluorine-labelled compounds
NZ600119A (en) Process and intermediates for the preparation of 5-biphenyl-4-yl-2-methylpentanoic acid derivatives
WO2010080353A8 (en) Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions
WO2009081152A3 (en) Antimicrobial compounds
WO2009047313A3 (en) Method of producing 2&#39; -deoxy-5-azacytidine (decitabine)
NZ598172A (en) Synthesis of boronic ester and acid compounds
WO2010147965A3 (en) Process for production of heterodimers of glutamic acid
WO2006127893A3 (en) Processes for production of 4-(biphenylyl)azetidin-2-one phosphonic acids
WO2009083532A3 (en) Novel method for the preparation of derivatives of dihydrotetraazapentacenes, products such as obtained, and uses thereof
EP2116549A3 (en) Novel phosphorus-containing compounds and their preparing process and use
CY1111904T1 (en) PROCEDURES FOR PREPARATIVE PRODUCTION AND RELATED INTERMEDIATE UNIONS
ZA201007977B (en) Process of preparing derivatives of 1-(2-halobiphenyl-4-yl)-cyclopropanecarboxylic acid
EP2665705A4 (en) IMPROVED METHOD FOR THE PRODUCTION OF MOLYBDEN-SUCCINIMIDE COMPLEXES OF HIGH MOLECULAR WEIGHT
EP1279665A3 (en) A process for the preparation of perindopril, its analogous compounds and salts thereof using 2,5-dioxo-oxazolidine intermediate compounds
WO2010002528A3 (en) Hydrofluoroacetal compounds and processes for their preparation and use
DE602006021411D1 (en) PROCESS FOR PREPARING OPTIONAL 2-SUBSTITUTED 1,6-DIHYDRO-6-OXO-4-PYRIMIDINCARBOXYLIC ACIDS
WO2011004389A3 (en) An improved process for the preparation of elvitegravir
JP2011526896A5 (en)
ATE489356T1 (en) ASYMMETRIC COPPER COMPLEX AND ITS USE IN CYCLOPROPANATION REACTION
NO20054100L (en) Process for the preparation of acid addition salts
ATE441627T1 (en) METHOD FOR PRODUCING VALSARTAN
ATE532516T1 (en) METHOD FOR SYNTHESIS OF GLYT-1 INHIBITORS
ATE527270T1 (en) PRODUCTION OF ORGANOSILANE ESTERS
WO2008111563A1 (en) Process for production of optically active sulfoxide compound using iron-salan complex catalyst
WO2007143014A3 (en) Methods for preparing glutamic acid derivatives and intermediates thereof

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09784699

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09784699

Country of ref document: EP

Kind code of ref document: A2