IP Library › Granted Patent US 8,288,398

Granted Patent B2

US 8,288,398 · App. 12/096,110 · Granted Oct 16, 2012

Antiproliferative pyrimidyl, fused pyrimidyl and pyrimidyl hydrazones

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 8,288,398
App. No.: 12/096,110
Granted: Oct 16, 2012
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present invention is related to a novel series of pyrimidyl or fused pyrimidyl hydrazones. Compounds of Formula (I) wherein A is selected from the group consisting of Formulas (A1), (A2), (A3), (A4), (A5) are useful for the treatment and/or prevention of a proliferative disease.

Claims (82)

1. A compound selected from the group consisting of:

N-Methyl-N′-(1-m-tolyl-ethylidene)-N-(2-trifluoromethy lquinazolin-4-yl)-hydrazine;

N-Methyl-N′-(1-p-tolyl-ethylidene)-N-(2-trifluoromethylquinazolin-4-yl)-hydrazine;

N-(1-p-Tolyl-ethylidene)-N′-(2-trifluoromethyl-quinazolin-4-yl)-hydrazine;

N-[1-(4-methoxy-phenyl)-ethylidene]-N′-(2-methyl-quinazolin-4-yl)-hydrazine;

N-(2-Methyl-quinazolin-4-yl)-N-(1-p-tolyl-ethylidene)-hydrazine;

N-(2-methyl-quinazolin-4-yl)-N′-(1-m-tolyl-ethylidene)-hydrazine;

N-Methyl-N-(2-methyl-quinazolin-4-yl)-N-(1-p-tolyl-ethylidene)-hydrazine;

Dimethyl-(4-{1-[(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]ethyl}-phenyl) amine;

[4-(1-{[6-(2-Methoxy-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine;

[4-(1-{[6-(3,5-dimethyl-isoxazol-4-yl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine;

Dimethyl-[4-(1-{[2-methyl-6-(2-trifluoromethoxy-phenyl)-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-amine;

[4-(1-{[6-(2-Isopropoxy-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine;

[4-(1-{[6-(2-Fluoro-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine;

[4-(1-{[6-(2-amino-phenyl)-2-methyl-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]-dimethylamine;

(4-{1-[(2-Methoxy-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-dimethylamine;

[4-(1{[2-Ethyl-6-(2-methoxy-phenyl)-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl]dimethylamine;

[4-(1-{[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-hydrazono}-ethyl)-phenyl] dimethyl amine;

Methyl-(4-{1-[(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-amine;

4-({1-[(2-Methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-thiourea;

N-(4-{1-[(2-Methyl-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-acetamide;

2-Methyl-4-{N′-[1-(4-methylamino-phenyl)-ethylidene]-hydrazino}-6-phenyl-pyrimidin-5-ylamine;

N-(2-Methyl-6-phenyl-pyrimidin-4-yl)-N′-[1-p-tolyl-propylidene]-hydrazine;

N-[1-(4-Chloro-phenyl)ethylidene]-N′-(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazine;

N-[1-(4-Methoxy-phenyl)-ethylidene]-N′-(2-methyl-6-phenyl-pyrimidin-4-yl)-hydrazine;

N-[6-(2-Methoxy-phenyl)-pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

N-[2-Ethyl-6-(2-methoxy-phenyl)-pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

N-[6-(2-Fluoro-phenyl)-2-methyl-pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

N-[6-(3-Methoxy-phenyl)-2-methyl pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine

N-[6-(2-Methoxy-phenyl)-2-methyl pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

N-[6-(4-Methoxy-phenyl)-2-methyl pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

2-(2-Methyl-6-{N′-[1-p-tolyl-ethylidene]-hydrazino}-pyrimidin-4-yl)-benzonitrile;

N-[6-(2-methyl-phenyl)-2-methyl-pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine;

N-[2-Methyl-6-(2-morpholin-4-yl-phenyl)-pyrimidin-4-yl]-N′[1-p-tolyl-ethylidene]-hydrazine;

N-[2-(2-Methyl-6-{N′-[1-p-tolyl-ethylidene]-hydrazino}-pyrimidin-4-yl)-phenyl]-acetamide;

[2-(2-Methyl-6-{N′-[1-p-tolyl-ethylidene]-hydrazino}-pyrimidin-4-yl)-phenyl]-methanol;

N-[6-(3,5-Dimethyl-isoxazol-4-yl)-2-methyl-pyrimidin-4-yl]-N′[1-p-tolyl-ethylidene]-hydrazine;

N-(2-Methyl-6-pyridin-3-yl-pyrimidin-4-yl)-N′-[1-p-tolyl-ethylidene]-hydrazine;

2-(2-Methyl-6-{N′-[1-p-tolyl-ethylidene]-hydrazino}-pyrimidin-4-yl)-phenylamine;

N-Methyl-N-(2-methyl-6-phenyl-pyrimidin-4-yl)-N′-[1-p-tolyl-ethylidene]-hydrazine; and

N-[6-(2,6-Dimethoxy-phenyl)-2-methyl-pyrimidin-4-yl]-N′-[1-p-tolyl-ethylidene]-hydrazine.

2. A pharmaceutical composition comprising a pharmaceutically acceptable carrier, diluent or excipient thereof and at least one compound selected from the group consisting of:

N-Methyl-N′-(1-m-tolyl-ethylidene)-N-(2-trifluoromethylquinazolin-4-yl)-hydrazine;