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1. WO1996002502 - PREPARATION OF BENZINDOLE COMPOUNDS FROM NAPHTHALENE COMPOUNDS

Publication Number WO/1996/002502
Publication Date 01.02.1996
International Application No. PCT/US1995/008958
International Filing Date 18.07.1995
Chapter 2 Demand Filed 16.02.1996
IPC
C07C 255/58 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
255Carboxylic acid nitriles
49having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
58containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
C07D 209/90 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
209Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
56Ring systems containing three or more rings
80- or -condensed
90Benzo indoles; Hydrogenated benzo indoles
CPC
C07C 255/58
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
255Carboxylic acid nitriles
49having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
58containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
C07D 209/90
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
209Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
56Ring systems containing three or more rings
80[b, c]- or [b, d]-condensed
90Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Applicants
  • AGOURON PHARMACEUTICALS, INC. [US/US]; 10350 North Torrey Pines Road La Jolla, CA 92037, US
Inventors
  • VARNEY, Michael, D.; US
  • PALMER, Cindy, L.; US
  • DEAL, Judy, G.; US
Agents
  • GARRETT, Arthur, S. ; Finnegan, Henderson, Farabow, Garrett & Dunner 1300 I Street, N.W. Washington, DC 20005-3315, US
Priority Data
08/276,92919.07.1994US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PREPARATION OF BENZINDOLE COMPOUNDS FROM NAPHTHALENE COMPOUNDS
(FR) PREPARATION DE COMPOSES DE BENZINDOLE A PARTIR DE COMPOSES DE NAPHTALENE
Abstract
(EN)
The invention relates to a process for preparing a substituted 2-amino-benz[cd]indole of formula (I). The nitro group of a substituted 1-nitro-8-cyano-naphthalene compound is reduced to an amine group to form a substituted 1-amino-8-cyano-naphthalene compound, which is cyclized to form the substituted 2-amino-benz[cd]indole. The reduction and cyclization may be effected in a one-pot procedure using a reducing agent such as stannous chloride, which generates an acid that cyclizes the reduction product. The syntheses of the 1-nitro-8-cyano-naphthalene compound and its precursors are also described.
(FR)
L'invention concerne un procédé de préparation d'un 2-amino-benz[cd]indole substitué de formule (I). On réduit le groupe nitro d'un composé 1-nitro-8-cyano-naphtalène en groupe amine pour former un composé 1-amino-8-cyano-naphtalène substitué que l'on cyclise pour former le 2-amino-benz[cd]indole substitué. La réduction et la cyclisation peuvent s'effectuer selon une technique en un seul pot au moyen d'un agent de réduction tel que le chlorure stanneux qui génère un acide cyclisant le produit de réduction. Les synthèses du composé 1-nitro-8-cyano-naphtalène et de ses précurseurs sont également décrites.
Also published as
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