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HK1099020A1 - Method of preparing 3-fluorinated quinolines - Google Patents

Method of preparing 3-fluorinated quinolines

Info

Publication number
HK1099020A1
HK1099020A1 HK07106501.2A HK07106501A HK1099020A1 HK 1099020 A1 HK1099020 A1 HK 1099020A1 HK 07106501 A HK07106501 A HK 07106501A HK 1099020 A1 HK1099020 A1 HK 1099020A1
Authority
HK
Hong Kong
Prior art keywords
alkyl
optionally substituted
protecting group
quinolines
fluoro
Prior art date
Application number
HK07106501.2A
Inventor
Youssef El-Ahmad
Jean-Pierre Leconte
Joel Malpart
Serge Mignani
Stephane Mutti
Michel Tabart
Original Assignee
Novexel
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 Novexel filed Critical Novexel
Publication of HK1099020A1 publication Critical patent/HK1099020A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • A61P31/04—Antibacterial agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Preparation of 3-fluoro-quinolines (I) (optionally substituted in the 5-, 6-, 7- and/or 8-position) involves heating a corresponding quinoline-3-diazonium tetrafluoroborate (II) in an inert organic solvent. Preparation of 3-fluoro-quinolines of formula (I) involves heating a quinoline-3-diazonium tetrafluoroborate of formula (II) in an inert organic solvent. [Image] R 1 - R 4H or F; linear, branched or cyclic alkyl (optionally substituted by 1-3 F, by OR 5 or by NR'R''); OR 6, NR' 1R'' 1 or COOR a; or phenyl or heteroaryl, both optionally substituted by one or more of the substituents given above or below; R 5H, alkyl or hydroxy-protecting group; R', R'' : H, alkyl or amino-protecting group; R 6H, phenol protecting group or alkyl (optionally substituted by 1-3 F, by OR 5 or by NR'R''); R' 1, R'' 1as for R', R''; or alkyl substituted by 1-3 F, by OR 5 or by NR'R''; and R aH, alkyl or carboxy-protecting group. An independent claim is included for (II) as new compounds.
HK07106501.2A 2003-11-17 2007-06-16 Method of preparing 3-fluorinated quinolines HK1099020A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0313384A FR2862301B1 (en) 2003-11-17 2003-11-17 NEW PROCESS FOR THE PREPARATION OF 3-FLUORINATED QUINOLINES
PCT/FR2004/002910 WO2005049575A1 (en) 2003-11-17 2004-11-15 Novel method of preparing 3-fluorinated quinolines

Publications (1)

Publication Number Publication Date
HK1099020A1 true HK1099020A1 (en) 2007-08-03

Family

ID=34508487

Family Applications (1)

Application Number Title Priority Date Filing Date
HK07106501.2A HK1099020A1 (en) 2003-11-17 2007-06-16 Method of preparing 3-fluorinated quinolines

Country Status (18)

Country Link
EP (1) EP1687276B1 (en)
JP (1) JP4751333B2 (en)
KR (1) KR20060123161A (en)
CN (1) CN100537540C (en)
AT (1) ATE445605T1 (en)
AU (1) AU2004291376A1 (en)
CA (1) CA2542796C (en)
DE (1) DE602004023640D1 (en)
ES (1) ES2334796T3 (en)
FR (1) FR2862301B1 (en)
HK (1) HK1099020A1 (en)
HR (1) HRP20060168A2 (en)
IL (1) IL175649A (en)
IS (1) IS8423A (en)
MX (1) MXPA06005599A (en)
NO (1) NO20062761L (en)
RU (1) RU2351591C2 (en)
WO (1) WO2005049575A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7396934B2 (en) 2003-11-17 2008-07-08 Youssef El-Ahmad Process for preparing 3-fluoroquinolines
US8716280B2 (en) 2009-01-21 2014-05-06 Basilea Pharmaceutica Ag Bicyclic antibiotics
CN104672131B (en) * 2013-11-27 2017-03-15 中国科学院大连化学物理研究所 A kind of method of 3 fluorine quinolines of synthesis

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA801526B (en) * 1979-03-26 1981-08-26 Robins Co Inc A H 4-amino-3-quinolinecarboxylic acids and esters-antisecretory, anti-ulcer compounds
DE3620856A1 (en) * 1986-06-21 1987-12-23 Basf Ag 3-CYANCHINOLINE DERIVATIVES
DK273689A (en) * 1988-06-06 1989-12-07 Sanofi Sa 4-AMINO-3-CARBOXYQUINOLINES AND -NAPHTHYRIDINES, PROCEDURES FOR THEIR PREPARATION AND USE OF THEM IN PHARMACEUTICALS
JPH06287187A (en) * 1993-04-02 1994-10-11 Nippon Soda Co Ltd New pyrazole derivative and its abricultural and horticultural germicide
SE0004056D0 (en) * 2000-11-06 2000-11-06 Astrazeneca Ab N-type calcium channel antagonists for the treatment of pain
FR2816618B1 (en) * 2000-11-15 2002-12-27 Aventis Pharma Sa HETEROCYCLYLALCOYL PIPERIDINE DERIVATIVES, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
FR2822154B1 (en) * 2001-03-13 2005-10-21 Aventis Pharma Sa QUINOLYL PROPYL PIPERIDINE DERIVATIVES, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
TWI275390B (en) * 2002-04-30 2007-03-11 Wyeth Corp Process for the preparation of 7-substituted-3- quinolinecarbonitriles

Also Published As

Publication number Publication date
JP4751333B2 (en) 2011-08-17
EP1687276B1 (en) 2009-10-14
DE602004023640D1 (en) 2009-11-26
FR2862301A1 (en) 2005-05-20
ES2334796T3 (en) 2010-03-16
WO2005049575A1 (en) 2005-06-02
CA2542796C (en) 2011-08-02
FR2862301B1 (en) 2007-12-21
ATE445605T1 (en) 2009-10-15
EP1687276A1 (en) 2006-08-09
AU2004291376A1 (en) 2005-06-02
IL175649A (en) 2011-01-31
RU2351591C2 (en) 2009-04-10
NO20062761L (en) 2006-08-17
MXPA06005599A (en) 2007-01-26
CA2542796A1 (en) 2005-06-02
IL175649A0 (en) 2006-09-05
RU2006120275A (en) 2008-01-10
JP2007511490A (en) 2007-05-10
CN100537540C (en) 2009-09-09
HRP20060168A2 (en) 2006-09-30
IS8423A (en) 2006-04-21
KR20060123161A (en) 2006-12-01
CN1894216A (en) 2007-01-10

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Legal Events

Date Code Title Description
PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)

Effective date: 20131115