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Thiazoleamide compound and medical application thereof in treating malignant tumor

A technology of thiazole amides and compounds, which is applied in the field of preparation of anti-cancer drugs, can solve the problems of affecting bioavailability, low water solubility, large dosage, etc., and achieve effective bioavailability, high bioavailability, and high water solubility Effect

Inactive Publication Date: 2011-02-09
苏州得普医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, the compound represented by formula (I), that is, dasatinib, has a very obvious first-pass effect after oral administration, and its bioavailability is only about 14-34%. Therefore, its dosage is generally large, and to a certain extent Increased side effects and aggravated treatment costs for patients
In addition, the water solubility of dasatinib is very low, only 0.008mg / mL, which largely affects the formulation preparation and bioavailability of dasatinib

Method used

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  • Thiazoleamide compound and medical application thereof in treating malignant tumor
  • Thiazoleamide compound and medical application thereof in treating malignant tumor
  • Thiazoleamide compound and medical application thereof in treating malignant tumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] N-(2-chloro-6-methylphenyl)-2-[[6-[4-tert-butoxycarbonyl-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5 -thiazolecarboxamide, its structural formula is as follows:

[0041]

[0042] Above-mentioned compound can obtain by following synthetic route:

[0043]

[0044] The specific preparation process is as follows: while stirring, 1-tert-butoxycarbonyl-piperazine (2.83g, 15.19mmol) and N, N-diisopropylethylamine (3.77g, 32.8mmol) were slowly added dropwise to N- (2-Chloro-6-methyl-phenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5thiazolecarboxamide (5g, 12.68mmol) In 100mL sulfone solution, heat to 115°C, react under stirring for 18 hours, cool to room temperature, add water, precipitate out, stir at room temperature for 15 minutes, filter, wash with ethyl acetate to obtain a light brown powder, and then use ethyl acetate The ester was recrystallized to obtain 5.4 g of pure beige product (78.3% yield).

[0045] The obtained taupe product was subjected to elemen...

Embodiment 2

[0050] N-(2-chloro-6-methylphenyl)-2-[[6-[4-ethoxycarbonyl-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5- Thiazole carboxamide, the structural formula is as follows:

[0051]

[0052] The compound can be prepared by making N-(2-chloro-6-methyl-phenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5thiazolecarboxamide with 1-ethyl Oxycarbonyl-piperazine is obtained through a substitution reaction, and the specific preparation process can be referred to Example 1.

Embodiment 3

[0054] N-(2-chloro-6-methylphenyl)-2-[[6-[4-tert-butylcarbonyl-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5- Thiazole carboxamide, the structural formula is as follows:

[0055]

[0056] The compound can be obtained by making N-(2-chloro-6-methyl-phenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5thiazolecarboxamide with 1-tert Butylcarbonyl-piperazine is obtained through a substitution reaction, and the specific preparation process can be found in Example 1.

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Abstract

The invention relates to a thiazoleamide compound and medical application thereof in treating malignant tumor. The thiazoleamide compound is an ideal Bcr-Abl and Src protein tyrosine kinase inhibitor and shows favorable effects when used for treating the malignant tumors, such as chronic myeloid leukemia, acute myeloid leukemia, acute lymphocytic leukemia, myelodysplastic syndromes, lung cancers, ovarian cancers, prostatic cancers, soft tissue sarcomas, malignant gliomas, and the like, and meanwhile, the thiazoleamide compound has the advantages of less usage amount and side effect.

Description

technical field [0001] The invention relates to thiazole amide compounds and their application in the preparation of anti-malignant tumor drugs. Background technique [0002] Protein tyrosine kinase (PTK) activates downstream signaling proteins through phosphorylation, thereby regulating cellular responses. When signaling proteins are overactive, they cause abnormal cell growth and differentiation. Therefore, abnormal regulation of tyrosine kinases is closely related to the invasion and poor prognosis of many tumors, and is an important feature of malignant tumors. [0003] Known, the compound represented by formula (I), N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]- 2-Methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide (also known as dasatinib or BMS-354825) is a protein tyrosine kinase inhibitor, such as a Src kinase inhibitor, and can be used in For the treatment of immune and tumor diseases. The compounds represented by formula (I) are also BCR / A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P35/02A61P35/00C07D417/12A61K31/506
Inventor 殷建明朱惠霖
Owner 苏州得普医药科技有限公司
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