Diazaindole-dicarbonyl-piperazinyl antiviral agents

Inactive Publication Date: 2005-06-09
VIIV HEALTHCARE UK (NO 5) LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0243] Another embodiment of the present invention is a method for treating mammals infected with the HIV virus, comprising administering to said mammal an antiviral effective amount of a compound of Formula I, including pharmaceutically acceptable salts thereof, and one or more pharmaceutically acceptable carriers, excipients or diluents; optionally the compound of Formula I can be administered in combination with an antiviral effective amount of an AIDS treatment agent selected from the group consisting of: (a) an AIDS antiviral agent; (b) an anti-infective agent; (

Problems solved by technology

HIV-1 (human immunodeficiency virus-1) infection remains a major medical problem, with an estimated 42 million people infected worldwide at the end of 2002.
Each of these drugs can only transiently restrain viral replication if used alone.
However, when used in combination, these drugs have a profound effect on viremia and disease progression.
However, despite these impressive results, 30 to 50% of patients ultimately fail combination drug therapies.
Furthermore, the high replication rate and rapid turnover of HIV-1 combined with the frequent incorporation of mutations, leads to the appearance of drug-resistant variants and treatment failures when sub-optimal drug concentrations are present (Larder and Kemp; Gulick; Kuritzkes; Morris-Jones et al; Schinazi et

Method used

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  • Diazaindole-dicarbonyl-piperazinyl antiviral agents
  • Diazaindole-dicarbonyl-piperazinyl antiviral agents
  • Diazaindole-dicarbonyl-piperazinyl antiviral agents

Examples

Experimental program
Comparison scheme
Effect test

preparation of example 1

2-(4-Benzoyl-piperazin-1-yl)-3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-3-oxo-propionitrile (Compound 9)

[0516]

example 1

[0517] To a solution of acid chloride 7 (0.5 mmol) and cyanomethylpiperazine 8 (150 mg, 0.66 mmol) in THF (4 mL) stirring at −35° C. was slowly added a solution of 0.5 M KHMDS in toluene (3.2 mL, 1.6 mmol). The reaction mixture was stirred at −35° C. for 1 h, quenched with sat. aqueous NaHCO3 (50 mL) and extracted with EtOAc (2×50 mL). The combined organics were concentrated and the residue purified by prep HPLC to yield the ketocyano intermediate 9 (39 mg, 0.96 mmol, 19%) as a yellow solid. 1H NMR: (500 MHz, DMSO-d6) δ 8.80 (s, 0.5H), 8.80 (s, 0.5H), 8.65 (s, 0.5H), 8.64 (s, 0.5H), 7.50-7.36 (m, 5H), 4.82-4.77 (m, 1H) 3.80-3.25 (m, 4H) 3.02-2.55 (m, 4H); LC / MS: (ES+) m / z (M+H)+=407; HPLC Rt=0.94 min., column G, conditions B.

preparation of example 2

1-(4-Benzoyl-piperazin-1-yl)-2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-ethane-1,2-dione (Compound 10)

[0518]

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Abstract

The invention comprises substituted diazaindole-dicarbonyl-piperazinyl derivatives of general Formula I
wherein:
Q is selected from the group consisting of — may represent a bond; T is —C(O)— or —CH(CN)—; and
—Y— is selected from the group consisting of
compositions thereof and their use for treating HIV infection.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Provisional Application Ser. No. 60 / 525,624 filed Nov. 26, 2003.BACKGROUND OF THE INVENTION [0002] 1. Field of the Invention [0003] This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with new diazaindole derivatives that possess unique antiviral activity. More particularly, the present invention relates to compounds useful for the treatment of HIV and AIDS. [0004] 2. Background Art [0005] HIV-1 (human immunodeficiency virus-1) infection remains a major medical problem, with an estimated 42 million people infected worldwide at the end of 2002. The number of cases of HIV and AIDS (acquired immunodeficiency syndrome) has risen rapidly. In 2002, ˜5.0 million new infections were reported, and 3.1 million people died from AIDS. Currently available drugs for the treatment of HIV inc...

Claims

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Application Information

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IPC IPC(8): A61K31/5025A61K31/519C07D487/04
CPCC07D487/04A61P31/00A61P31/12A61P31/18A61P37/02A61K31/5025A61K31/519
Inventor BENDER, JOHNYANG, ZHONGKADOW, JOHNMEANWELL, NICHOLAS
Owner VIIV HEALTHCARE UK (NO 5) LTD
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