HIV inhibiting bicyclic pyrimidine derivatives

Patent metadata

Field	Value
Publication number	US-10072015-B2
Application number	US-201715713404-A
Country	US
Kind code	B2
Filing date	Sep 22, 2017
Priority date	Oct 29, 2004
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

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 selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof.

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

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof.

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

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof.

4. A composition comprising a therapeutically effective amount of a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
and a pharmaceutically acceptable carrier.

5. A composition of claim 4 , comprising a therapeutically effective amount of a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
and a pharmaceutically acceptable carrier.

6. A composition of claim 4 , comprising a therapeutically effective amount of a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
and a pharmaceutically acceptable carrier.

7. A process for preparing a composition as claimed in claim 4 , said process comprising mixing a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
with a carrier.

8. A process for preparing a composition as claimed in claim 4 , said process comprising mixing a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
with a carrier.

9. A process for preparing a composition as claimed in claim 4 , said process comprising mixing a compound selected from the group consisting of:

and an N-oxide; a pharmaceutically acceptable addition salt; a quaternary amine; or a stereochemically isomeric form thereof;
with a carrier.

Assignees

• 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

• C07D473/24

  one nitrogen and one sulfur atom · CPC title

• C07D473/00

  Heterocyclic compounds containing purine ring systems · CPC title

• C07D473/34

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

• C07D473/16

  two nitrogen atoms · CPC title

• A61P31/18

  for HIV · CPC title