HIV inhibiting bicyclic pyrimidine derivatives

Patent metadata

Field	Value
Publication number	US-9487518-B2
Application number	US-201213410779-A
Country	US
Kind code	B2
Filing date	Mar 2, 2012
Priority date	Oct 29, 2004
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

HIV replication inhibitors of formula

wherein
-a 1 =a 2 -a 3 =a 4 - is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; -b 1 =b 2 -b 3 =b 4 - is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; n and m is 0-4, R 1 is hydrogen; aryl; formyl; C 1-6 alkylcarbonyl; C 1-6 alkyl; C 1-6 alkyloxycarbonyl; R 2 is OH; halo; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; substituted carbonyl; carboxyl; CN; nitro; amino; polyhalomethyl; polyhalomethylthio; —S(═O) p R 6 ; C(═NH)R 6 ; R 2a is CN; amino; substituted amino; C 1-6 alkyl; halo; C 1-6 alkyloxy; carbonyl; —CH═N—NH—C(═O)—R 16 ; C 1-6 alkyloxyC 1-6 alkyl; C 2-6 alkenyl or C 2-6 alkynyl; —C(═N—O—R 8 )—C 1-4 alkyl; R 7 or —X—R 7 ; R 3 is CN; amino; C 1-6 alkyl; halo; C 1-6 alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R 16 ; substituted C 1-6 alkyl; C 1-6 alkyloxyC 1-6 alkyl; substituted C 2-6 alkenyl or C 2-6 alkynyl; —C(═N—O—R 8 )—C 1-4 alkyl; R 7 ; —X—R 7 ; R 4 is halo; OH; C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; C 3-7 cycloalkyl; C 1-6 alkyloxy; CN; nitro; polyhaloC 1-6 alkyl; polyhaloC 1-6 alkyloxy; substituted carbonyl; formyl; amino; mono- or di(C 1-4 alkyl)amino or R 7 ; -A-B— is —CR 5 ═N—, —N═N—, —CH 2 —CH 2 —, —CS—NH—, —CO—NH—, —CH═CH—; and the use of these compounds for the prevention or the treatment of HIV infection.

First claim

The invention claimed is:

1. A compound of formula

wherein R 2a is cyano, R 3 is ethenyl substituted with cyano, R 4 is —CH 3 or halo, and -A-B— is a radical —N═N— (c-2), N-oxides, pharmaceutically acceptable addition salts, quaternary amines or stereoisomeric forms thereof.

2. A compound of claim 1 , selected from the group consisting of:

and
N-oxides, pharmaceutically acceptable addition salts, quaternary amines or stereoisomeric forms thereof.

3. A composition comprising: a therapeutically effective amount of

and a pharmaceutically acceptable carrier.

4. A process for preparing a composition as claimed in claim 3 , said process comprising mixing a compound selected from:

with the carrier.

Assignees

• Guillemont Jerôme Emile Georges
• Paugam Mikaël
• Delest Bruno Francois Marie
• Heeres Jan
• Lewi Paulus Joannes
• Janssen Paul Adriaan Jan
• Arts Frank Xavier Jozef Herwig
• Janssen Sciences Ireland Uc

Inventors

• Guillemont Jerôme Emile Georges
• Paugam Mikaël
• Delest Bruno Francois Marie
• Heeres Jan
• Lewi Paulus Joannes
• Janssen Paul Adriaan Jan

Classifications

• C07D473/34

  attached in position 6, e.g. adenine · CPC title

• A61P31/18

  for HIV · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D473/00 Primary

  Heterocyclic compounds containing purine ring systems · CPC title

• C07D473/16

  two nitrogen atoms · CPC title