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Tricyclic azole derivatives, their manufacture and use as pharmaceutical agents

A compound and heterocyclic group technology, applied in the field of tricyclic pyrrole derivatives, can solve the problems of tumor cell programmed cell death and other problems

Inactive Publication Date: 2008-04-09
F HOFFMANN LA ROCHE & CO AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, specific inhibition of Aurora kinases by selective inhibitors is thought to stop uncontrolled proliferation, reestablish mitotic checkpoint control and lead to programmed cell death in tumor cells

Method used

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  • Tricyclic azole derivatives, their manufacture and use as pharmaceutical agents
  • Tricyclic azole derivatives, their manufacture and use as pharmaceutical agents
  • Tricyclic azole derivatives, their manufacture and use as pharmaceutical agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0462] 7,7-Dimethyl-2-(1,4,5,6-tetrahydro-cyclopentadienopyrazol-3-yl)-5,7-dihydro-3H-imidazo[4,5 -f]indol-6-one

[0463] 5,6-diamino-3,3-dimethyl-1,3-dihydro-indol-2-one (143mg, 0.75mmol), and 1,4,5,6-tetrahydro-cyclopenta Dienopyrazole-3-carboxylic acid (114 mg, 0.75 mmol) was mixed with polyphosphoric acid (5.10 g, 53.12 mmol) and phosphorus pentoxide (190 mg, 1.34 mmol), and stirred at 150° C. under nitrogen for 6 hours. The mixture was quenched with ice water (25ml) and the resulting solution was adjusted to pH 7-8 by addition of ammonia, then extracted twice with ethyl acetate (3 x 50ml). The combined organic layers were washed with water (50ml), dried over sodium sulfate and concentrated. The crude product was purified by HPL chromatography. Yield: 37 mg (16%) of light brown solid.

[0464] MS: M=308.1(API+)

[0465] 1 H-NMR (400MHz, D 6 -DMSO): (ppm) = 1.29 (s, 6H), 2.52 (m, 2H), 2.71 (m, 2H), 2.81 (m, 2H), 6.88 (br, 1H), 6.95 (br, 1H), 10.23 (br, 1H)

Embodiment 2

[0467] 5,7,7-Trimethyl-2-(1,4,5,6-tetrahydro-cyclopentadienopyrazol-3-yl)-5,7-dihydro-3H-imidazo[4 , 5-f]indol-6-one

[0468] In a manner similar to that described for Example 1, 5,7,7-trimethyl-2-(1,4,5,6-tetrahydro-cyclopentadienopyrazol-3-yl)-5 , 7-dihydro-3H-imidazo[4,5-f]indol-6-ones were prepared from appropriate starting materials.

[0469] MS: M=322.0(API+)

[0470] 1 H-NMR (400MHz, D 6 -DMSO): (ppm) = 1.31 (s, 6H), 2.52 (m, 2H), 2.71 (m, 2H), 2.81 (m, 2H), 3.19 (s, 3H), 6.95 and 7.23 (s, 1H , two tautomeric forms), 7.39 and 7.61 (s, 1H, two tautomeric forms), 12.48 (br, 1H), 12.70 (br, 1H)

Embodiment 3

[0472] 5-Ethyl-7,7-dimethyl-2-(1,4,5,6-tetrahydro-cyclopentadienopyrazol-3-yl)-5,7-dihydro-3H-imidazole And[4,5-f]indol-6-one

[0473] In a manner similar to that described for Example 1, 5-ethyl-7,7-dimethyl-2-(1,4,5,6-tetrahydro-cyclopentadienopyrazol-3-yl )-5,7-dihydro-3H-imidazo[4,5-f]indol-6-ones were prepared from appropriate starting materials.

[0474] MS: M=336.2(API+)

[0475] 1 H-NMR (400MHz, D 6 -DMSO): (ppm) = 1.18 (t, 3H), 1.31 (s, 6H), 2.55 (m, 2H), 2.70 (m, 2H), 2.81 (m, 2H), 3.76 (q, 2H), 6.98 and 7.27 (s, 1H, two tautomeric forms), 7.37 and 7.61 (s, 1H, two tautomeric forms), 12.50 (br, 1H), 12.75 (br, 1H)

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Abstract

Objects of the present invention are the compounds of formula (I), their pharmaceutically acceptable salts, enantiomeric forms, diastereoisomers and racemates, the preparation of the above mentioned compounds, medicaments containing them and their manufacture, as well as the use of the above mentioned compounds in the control or prevention of illnesses such as cancer.

Description

[0001] The present invention relates to novel tricyclic pyrrole derivatives, processes for their preparation, pharmaceutical compositions containing them and their preparation, and the use of these compounds as pharmaceutically active agents. Background of the invention [0002] Protein kinases regulate many different signaling processes by adding phosphate groups to proteins (Hunter, T., Cell 50 (1987) 823-829); in particular serine / threonine Phosphorylates proteins on alcohol moieties. The serine / threonine kinase family includes members that control cell growth, migration, differentiation, gene expression, muscle contraction, glucose metabolism, cellular protein synthesis, and cell cycle regulation. [0003] Aurora kinases are a family of serine / threonine kinases thought to play a key role in protein phosphorylation events that are necessary for the completion of fundamental mitotic events. The Aurora kinase family consists of three key members: Aurora A, B and C (also know...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/4188A61P35/00A61P43/00C07D209/00C07D235/00
CPCC07D519/00C07D487/04A61P11/06A61P25/00A61P25/28A61P29/00A61P35/00A61P37/06A61P43/00A61P9/00
Inventor 吉·乔治伯恩哈德·戈勒汉斯-威利·克雷尔安雅·利姆戈乌尔丽克·赖夫彼德拉·吕格尔马蒂亚斯·吕特
Owner F HOFFMANN LA ROCHE & CO AG
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