Title:
PYRIDINONE AND PYRIDINETHIONE DERIVATIVES HAVING HIV INHIBITING PROPERTIES
Document Type and Number:
WIPO Patent Application WO2002024650
Kind Code:
A3
Abstract:
The present invention is concerned among others with compounds of formula (1), the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and stereochemically isomeric forms thereof, wherein Q is halo, C1-6 alkyl or C2-6 alkenyl; X is (a-2) with q and r being O and Z being O, S or SO; R1 is aryl; R2 is selected from formyl; C1-6alkyloxycarbonylalkyl; Het<2>; Het<2>C1-6alkyl, C1-6alkylthio; C1-6alkyl optionally substituted with one or two substituents each independently selected from hydroxy, and halo; R3 is selected from formyl; C1-6alkyl optionally substituted with one or two C1-6alkyloxy; R4 is hydrogen, with HIV inhibiting properties.
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| WO/2008/123469 | SIX-MEMBERED AMIDE COMPOUND AND USE THEREOF |
Inventors:
GUILLEMONT JEROME (FR)
BENJAHAD ABDELLAH (FR)
MABIRE DOMINIQUE (FR)
N GUYEN CHI HUNG (FR)
GRIERSON DAVID (FR)
MONNERET CLAUDE (FR)
BISAGNI EMILE (FR)
SANZ GERARD (FR)
DECRANE LAURENCE (FR)
BENJAHAD ABDELLAH (FR)
MABIRE DOMINIQUE (FR)
N GUYEN CHI HUNG (FR)
GRIERSON DAVID (FR)
MONNERET CLAUDE (FR)
BISAGNI EMILE (FR)
SANZ GERARD (FR)
DECRANE LAURENCE (FR)
Application Number:
PCT/IB2001/002082
Publication Date:
August 08, 2002
Filing Date:
September 18, 2001
Export Citation:
Assignee:
JANSSEN PHARMACEUTICA NV (BE)
CENTRE NAT RECH SCIENT (FR)
INST CURIE (FR)
GUILLEMONT JEROME (FR)
BENJAHAD ABDELLAH (FR)
MABIRE DOMINIQUE (FR)
N GUYEN CHI HUNG (FR)
GRIERSON DAVID (FR)
MONNERET CLAUDE (FR)
BISAGNI EMILE (FR)
SANZ GERARD (FR)
DECRANE LAURENCE (FR)
CENTRE NAT RECH SCIENT (FR)
INST CURIE (FR)
GUILLEMONT JEROME (FR)
BENJAHAD ABDELLAH (FR)
MABIRE DOMINIQUE (FR)
N GUYEN CHI HUNG (FR)
GRIERSON DAVID (FR)
MONNERET CLAUDE (FR)
BISAGNI EMILE (FR)
SANZ GERARD (FR)
DECRANE LAURENCE (FR)
International Classes:
A61K31/428; A61K31/4365; A61K31/4412; A61K31/443; A61K31/4439; A61K31/444; A61K31/453; A61K31/454; A61K31/4545; A61K31/47; A61K31/4709; A61K31/496; A61K31/497; A61K31/506; A61K31/5377; A61K31/541; A61K31/675; A61K45/00; A61P31/18; C07D213/64; C07D213/69; C07D213/70; C07D213/71; C07D213/75; C07D213/78; C07D213/80; C07D213/81; C07D213/82; C07D213/84; C07D213/85; C07D213/89; C07D215/22; C07D215/227; C07D215/36; C07D221/04; C07D401/04; C07D401/06; C07D401/12; C07D401/14; C07D405/04; C07D405/06; C07D405/12; C07D405/14; C07D407/04; C07D407/06; C07D407/12; C07D407/14; C07D409/04; C07D409/12; C07D413/06; C07D413/12; C07D413/14; C07D417/06; C07D417/12; C07D471/04; C07D491/04; C07D495/04; C07F9/59; C07F9/6584; (IPC1-7): C07D401/12; C07D213/78; C07D407/06; C07D417/06; C07D401/06; C07D213/71; C07D405/04; C07D213/82; C07D213/70; C07D213/69; C07D409/12; C07D417/12; C07D405/12; C07D491/04; C07D215/22
Domestic Patent References:
| WO1997005113A1 | 1997-02-13 | |||
| WO1999055676A1 | 1999-11-04 | |||
| WO1997037977A1 | 1997-10-16 | |||
| WO2000000475A1 | 2000-01-06 |
Other References:
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DATABASE CAOLD [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KOLDER C.R. ET AL: "Tautomerism of Hydroxypyridines - (II) Bromination of 2,4-Dihydroxypyridines and its Ethyl Derivatives", XP002190994, retrieved from STN Database accession no. CA55:1608f
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RAN, CHONG-ZHAO ET AL: "Synthesis and bio-activity study of the 2(1H)-quinolone compounds", XP002190976, retrieved from STN Database accession no. 134:56548
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; STADLBAUER, WOLFGANG: "Synthesis of 4-azido-2(1H)-quinolones", XP002190977, retrieved from STN Database accession no. 107:134174
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; EARL, RICHARD A. ET AL: "The preparation of 2(1H)-pyridinones and 2,3-dihydro-5(1H)- indolizinones via transition metal mediated cocyclization of alkynes and isocyanates. A novel construction of the antitumor agent camptothecin", XP002190978, retrieved from STN Database accession no. 102:6913
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; EARL, RICHARD A. ET AL: "Cobalt-catalyzed cocyclizations of isocyanato alkynes: a regiocontrolled entry into 5-indolizinones. Application to the total synthesis of camptothecin", XP002190979, retrieved from STN Database accession no. 100:85968
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; FITTON, ALAN O. ET AL: "Reactions of formylchromone derivatives. Part 1. Cycloadditions to 2- and 3-(aryliminomethyl)chromones", XP002190980, retrieved from STN Database accession no. 88:22533
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MOSHCHITSKII, S. D. ET AL: "Reactions of diethyl 2,3,5,6-tetrachloro-4-pyridylmalonate", XP002190981, retrieved from STN Database accession no. 73:120466
MAO C ET AL: "Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyr idyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,GB,OXFORD, vol. 9, no. 11, 7 June 1999 (1999-06-07), pages 1593 - 1598, XP004169626, ISSN: 0960-894X
DATABASE CAOLD [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KOLDER C.R. ET AL: "Tautomerism of Hydroxypyridines - (II) Bromination of 2,4-Dihydroxypyridines and its Ethyl Derivatives", XP002190994, retrieved from STN Database accession no. CA55:1608f
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RAN, CHONG-ZHAO ET AL: "Synthesis and bio-activity study of the 2(1H)-quinolone compounds", XP002190976, retrieved from STN Database accession no. 134:56548
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; STADLBAUER, WOLFGANG: "Synthesis of 4-azido-2(1H)-quinolones", XP002190977, retrieved from STN Database accession no. 107:134174
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; EARL, RICHARD A. ET AL: "The preparation of 2(1H)-pyridinones and 2,3-dihydro-5(1H)- indolizinones via transition metal mediated cocyclization of alkynes and isocyanates. A novel construction of the antitumor agent camptothecin", XP002190978, retrieved from STN Database accession no. 102:6913
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; EARL, RICHARD A. ET AL: "Cobalt-catalyzed cocyclizations of isocyanato alkynes: a regiocontrolled entry into 5-indolizinones. Application to the total synthesis of camptothecin", XP002190979, retrieved from STN Database accession no. 100:85968
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; FITTON, ALAN O. ET AL: "Reactions of formylchromone derivatives. Part 1. Cycloadditions to 2- and 3-(aryliminomethyl)chromones", XP002190980, retrieved from STN Database accession no. 88:22533
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MOSHCHITSKII, S. D. ET AL: "Reactions of diethyl 2,3,5,6-tetrachloro-4-pyridylmalonate", XP002190981, retrieved from STN Database accession no. 73:120466
MAO C ET AL: "Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyr idyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,GB,OXFORD, vol. 9, no. 11, 7 June 1999 (1999-06-07), pages 1593 - 1598, XP004169626, ISSN: 0960-894X
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