EP0603324A1 - Verfahren zur herstellung des rechsdrehenden isomers eines isoindolinonderivats - Google Patents

Verfahren zur herstellung des rechsdrehenden isomers eines isoindolinonderivats

Info

Publication number
EP0603324A1
EP0603324A1 EP92920565A EP92920565A EP0603324A1 EP 0603324 A1 EP0603324 A1 EP 0603324A1 EP 92920565 A EP92920565 A EP 92920565A EP 92920565 A EP92920565 A EP 92920565A EP 0603324 A1 EP0603324 A1 EP 0603324A1
Authority
EP
European Patent Office
Prior art keywords
formula
dextrorotatory isomer
preparing
dextrorotatory
isoindolinone
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
EP92920565A
Other languages
English (en)
French (fr)
Inventor
André Busson
Christophe Daubie
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.)
Aventis Pharma SA
Original Assignee
Rhone Poulenc Rorer SA
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 Rhone Poulenc Rorer SA filed Critical Rhone Poulenc Rorer SA
Publication of EP0603324A1 publication Critical patent/EP0603324A1/de
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives

Definitions

  • the present invention relates to a process for the preparation of the dextrorotatory isomer of the isoindolinone derivative of formula:
  • the dealkoxycarbonylation of the menthyl ester of formula (II) is carried out by the action of a strong mineral acid at a temperature in the region of 0 ° C. It is particularly advantageous, to obtain a satisfactory enantioselectivity, to use concentrated sulfuric acid.
  • Condensation is generally carried out in an organic solvent in the presence of a base.
  • organic solvent dimethylformamide, racetonitrile, dimethyl sulfoxide, aromatic hydrocarbons (benzene, toluene) or N-methylpyrrolidone are generally used.
  • a base an alkali metal carbonate (sodium, potassium) or a hydride such as sodium hydride is generally used.
  • the reaction is carried out at a temperature between 0 and 50 ° C.
  • the product of formula (IV) can be obtained by chlorination of the product of formula:
  • the product of formula (V) can be obtained according to the method described, for example, in Belgian patent BE 835325.
  • the ⁇ -ketoester of formula (HI) can be obtained according to the method described by

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP92920565A 1991-09-09 1992-09-07 Verfahren zur herstellung des rechsdrehenden isomers eines isoindolinonderivats Ceased EP0603324A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9111101 1991-09-09
FR9111101A FR2681068B1 (fr) 1991-09-09 1991-09-09 Procede de preparation de l'isomere dextrogyre d'un derive de l'isoindolinone.
PCT/FR1992/000848 WO1993005041A1 (fr) 1991-09-09 1992-09-07 Procede de preparation de l'isomere dextrogyre d'un derive de l'isoindolinone

Publications (1)

Publication Number Publication Date
EP0603324A1 true EP0603324A1 (de) 1994-06-29

Family

ID=9416751

Family Applications (2)

Application Number Title Priority Date Filing Date
EP92402442A Pending EP0534814A1 (de) 1991-09-09 1992-09-07 Verfahren zur Herstellung eines rechtsdrehenden Isomeren eines Derivats des Isoindolins
EP92920565A Ceased EP0603324A1 (de) 1991-09-09 1992-09-07 Verfahren zur herstellung des rechsdrehenden isomers eines isoindolinonderivats

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP92402442A Pending EP0534814A1 (de) 1991-09-09 1992-09-07 Verfahren zur Herstellung eines rechtsdrehenden Isomeren eines Derivats des Isoindolins

Country Status (6)

Country Link
EP (2) EP0534814A1 (de)
JP (1) JPH07500094A (de)
CA (1) CA2117196A1 (de)
FR (1) FR2681068B1 (de)
MX (1) MX9205115A (de)
WO (1) WO1993005041A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU783516B2 (en) 2001-04-30 2005-11-03 Warner-Lambert Company Methods, kits and compositions for using pyrrole derivatives
EP1490363B1 (de) 2002-03-29 2006-01-25 Indevus Pharmaceuticals, Inc. Verfahren zur herstellung von 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinon

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9305041A1 *

Also Published As

Publication number Publication date
WO1993005041A1 (fr) 1993-03-18
MX9205115A (es) 1993-04-01
CA2117196A1 (fr) 1993-03-18
FR2681068A1 (fr) 1993-03-12
FR2681068B1 (fr) 1993-11-19
EP0534814A1 (de) 1993-03-31
JPH07500094A (ja) 1995-01-05

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