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Thiazole aminobenzamide acetic acid derivative and application thereof

An alkyl and benzyl technology, applied in the field of medicinal chemistry, can solve problems such as ineffective drug resistance

Active Publication Date: 2019-02-12
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented inventions provide novel chemicals that have anti-cancer properties but they still work well for some cancer types without causing side effects or affecting their overall healthy functioning negatively.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding new drugs or combination therapies aim towards improving cancer treatments without causing unwanted reactions like chemotherapy or radiation.

Method used

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  • Thiazole aminobenzamide acetic acid derivative and application thereof
  • Thiazole aminobenzamide acetic acid derivative and application thereof
  • Thiazole aminobenzamide acetic acid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1 (3-((5-methyl-4-phenylthiazol-2-yl) amino) benzoyl) glycine

[0057] Step a:

[0058]

[0059] Add 11.4341 g (0.12 mol) of ammonium thiocyanate and 20 mL of acetone into a 100 mL oblique-necked reaction flask equipped with mechanical stirring and a condenser, and stir evenly through mechanical stirring. 16.8034 g (0.13 mol) of benzoyl chloride was added dropwise (dropped in 10 min), and the solution changed from clear to white turbid. Heat to reflux, add 14.1147 g (0.10 mol) m-aminobenzoic acid in 4 batches, monitor the reaction process by TLC (ethyl acetate:petroleum ether = 4:1), and complete the reaction in 8 h. Cool, filter, and dry the obtained solid to obtain 28.0041 g of light yellow powder 3-(3-benzoylthioureido)benzoic acid, m.p. 184 ~ 186 ℃.

[0060] Add 0.9913 g (0.12 mol) of 3-(3-benzoylthioureido)benzoic acid and 33 mL of 10% NaOH into a 100 mL oblique-necked reaction flask with a condenser, the measured pH=13, magnetic stirring, and heati...

Embodiment 2

[0070] Example 2 (3-((5-methyl-4-(p-tolyl) thiazol-2-yl) amino) benzoyl) glycine

[0071]

[0072] The operation was the same as above to obtain 0.0934 g of brown powder, yield 61.28%, m.p.225-228°C. 1 H NMR (DMSO-D 6 , 400MHz), δ : 2.36 (s, 3H, CH 3 ), 2.41 (s, 3H, CH 3 ), 3.93(d, J = 8.0 Hz, 2H, NHCH 2 ), 7.26-8.08 (m, 8H, 2×C 6 h 4 ), 8.82(t, J = 8.0 Hz, 1H, CONH), 10.49 (s, 1H, COOH).

Embodiment 3

[0073] Example 3 3-((4-(4-chlorophenyl)-5-methylthiazol-2-yl)amino)benzoyl)glycine

[0074]

[0075] The operation was the same as above to obtain 0.09492 g of yellow powder, yield 59.18%, m.p.238-240°C. 1 H NMR (DMSO-D 6 , 400MHz), δ : 2.43 (s, 3H, CH 3 ), 3.91(d, J = 8.0 Hz, 2H, NHCH 2 ), 7.26-8.08 (m, 8H, 2×C 6 h 4 ), 8.75 (t, J = 8.0 Hz, 1H, CONH), 10.25 (s, 1H, COOH).

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Abstract

The invention discloses a thiazole aminobenzamide acetic acid derivative with anti-tumour activity, and the thiazole aminobenzamide acetic acid derivative can be used for preparing an anti-cancer drug, especially can be used as a Bcr-Abl tyrosine kinase inhibitor, and particularly can be used as a T315I mutation Bcr-Abl tyrosine kinase inhibitor of T315I mutation.

Description

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Claims

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Application Information

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Owner NANHUA UNIV
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