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Imidazolothiazole compounds for the treatment of disease

A compound, independent technology, applied in metabolic diseases, skin diseases, sensory diseases, etc., can solve problems such as RTK damage deactivation

Active Publication Date: 2009-06-03
AMBIT BIOSCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Finally, while hyperactivation of RTK signaling pathways is often the underlying principle of cancer, damaging inactivation of RTKs, such as through ligand-induced endocytosis or diminished downregulation of RTKs through damaging negative feedback loops, also may be the cause of some cancers

Method used

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  • Imidazolothiazole compounds for the treatment of disease
  • Imidazolothiazole compounds for the treatment of disease
  • Imidazolothiazole compounds for the treatment of disease

Examples

Experimental program
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Effect test

preparation example Construction

[0470] G. Compound Preparation

[0471] The starting materials of the synthetic examples provided by the present invention can be purchased through commercial channels, or obtained by literature methods (such as March Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, (1992) 4th Ed.; Wiley Interscience, New York ). All commercially available compounds were used without further purification unless otherwise stated. CDCl 3 (99.8% D, Cambridge Isotope Laboratories) was used in all experiments shown. Proton ( 1 h) The nuclear magnetic resonance (NMR) spectrum was recorded by a Bruker Avance 300 MHz NMR spectrometer. The list of notable peaks generally includes: number of protons, and multiplicity (s, singlet; d, doublet; t, triplet; q, quadruplet; m, multiplet; brs, broad singlet), chemical shift is It is described in parts per million (δ) relative to tetramethylsilane. Low resolution mass spectra (MS) were obtained as electrospray ionization (ESI) mass spectr...

Embodiment 1

[0531] Example 1: N-(5-tert-butyl-isoxazol-3-yl)-N'-imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl} Preparation of urea [compound A1]

[0532] A. Preparation of intermediate 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole. Dissolve 2-aminobenzothiazole (751 mg, 5 mmol) and 2-bromo-4'-nitroacetophenone (1.22 g, 5 mmol) in ethanol, and heat to reflux overnight. The solution was then cooled at room temperature for 24 hours. The precipitate was collected by filtration, washed with methanol and dried in vacuo.

[0533] B. Preparation of 2-(4-amino-phenyl)imidazo[2,1-b][1,3]benzothiazole. The intermediate from step A (428 mg, 1.5 mmol) was prepared as a suspension in isopropanol, to which iron powder (419 mg, 7.5 mmol) was added. The suspension was heated to reflux overnight with vigorous stirring. Completion of the reaction was confirmed by LCMS. 1N HCl was added to the mixture and allowed to cool to room temperature. The precipitate was collected by filtration and washed wit...

Embodiment 2

[0540] Example 2: 1-(5-tert-butyl-isoxazol-3-yl)-3-[4-(7-morpholin-4-yl-benzo[d]imidazo[2,1-b ]thiazol-2-yl)-phenyl]-urea preparation; [compound A6]

[0541] A. Preparation of intermediate 6-morpholin-4-yl-benzothiazol-2-amine: NH 4 SCN (2.28 g, 30 mmol) was added in small portions to a solution of 4-N-morpholinoaniline (1.78 g, 10 mmol) in acetic acid (20 mL). After stirring the mixture for 30 minutes, a solution of bromine in acetic acid (1.6 g in 5 mL) was added to the mixture, and the mixture was stirred at room temperature overnight. The mixture was then heated at 90 °C for 30 min, followed by cooling and washing with saturated NaHCO 3 Neutralize, then use CH 2 Cl 2 Extract 3 times. The combined organic phases were washed with MgSO 4 Dry and concentrate to dryness. Add 30 mL of 10% HCI to the residue, wash with saturated NaHCO 3 Neutralization afforded a tan solid (1.541 g, 66%).

[0542] B. Preparation of intermediate 7-morpholin-4-yl-2-(4-nitro-phenyl)-imidazo[...

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Abstract

The present invention provides compounds, compositions and methods for modulating the activity of receptor kinases and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by receptor kinases.

Description

[0001] This application claims priority to US Provisional Application No. 60 / 743,543, filed March 17, 2006, entitled "Imidazolothiazole Derivatives for the Treatment of Disease." The disclosures of the aforementioned referenced applications are hereby incorporated by reference in their entirety. field of invention [0002] The present invention provides novel small molecule compounds, compositions and methods for treating diseases. Provided compounds are modulators of enzymatic activity, such as kinases, which are useful in the treatment, prevention, or amelioration of diseases or conditions associated with enzymatic activity, or one or more symptoms thereof. Background technique [0003] Protein kinases (PKs) are enzymes that catalyze the phosphorylation of hydroxyl groups on tyrosine, serine and threonine residues of proteins. Protein kinases, especially the receptor protein tyrosine kinase (RTK) family of protein kinases, mainly serve as growth factor receptors and play ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
CPCC07D513/04A61K31/429A61K31/454A61K31/496A61K31/5377A61P1/04A61P11/00A61P11/06A61P13/12A61P17/02A61P19/02A61P19/10A61P25/00A61P27/16A61P29/00A61P31/00A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P5/14A61P9/10A61P3/10
Inventor 施里帕德·巴维特晁琪罗伯特·M·格罗兹菲尔德希特什·K·帕泰尔凯利·G·斯普兰克
Owner AMBIT BIOSCIENCES
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