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Thiazol-aminobenzamide acetate derivative and application thereof

A technology of alkyl and methyl, applied in the field of medicinal chemistry, can solve problems such as drug resistance that cannot be effectively solved, and achieve the effect of broadening the scope

Active Publication Date: 2019-03-12
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with imatinib, it can solve the drug resistance caused by most mutants, but it cannot effectively solve the drug resistance caused by the T315I mutation (Ann Oncol, 2007, 18 (6): 42-46; Eur J Cancer, 2010 , 46 (10): 1781-1789; Haematologica, 2014, 99(7): 1191-1196)

Method used

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  • Thiazol-aminobenzamide acetate derivative and application thereof
  • Thiazol-aminobenzamide acetate derivative and application thereof
  • Thiazol-aminobenzamide acetate derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 (3-((5-methyl-4-phenylthiazol-2-yl)amino)benzoyl)glycine methyl ester

[0059] Step a:

[0060]

[0061] 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 ℃.

[0062] 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, an...

Embodiment 2

[0069] Example 2 (3-((5-methyl-4-(p-tolyl)thiazol-2-yl)amino)benzoyl)glycine methyl ester

[0070]

[0071] The operation was the same as above to obtain 0.3018g of white powder, yield 68.23%, m.p.187 ~ 188°C. 1 H NMR (DMSO-D 6 , 400 MHz), δ : 2.36 (s, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 3.67(s, 3H, OCH 3 ), 4.02 (d, J = 4.0 Hz, 2H, NHCH 2 ), 7.26-8.07 (m, 8H, 2×C 6 h 4 ), 8.90 (t, J = 4.0, 1H, CONH), 10.30 (s, 1H, NH).

Embodiment 3

[0072] Example 3 3-((4-(4-chlorophenyl)-5-methylthiazol-2-yl)amino)benzoyl)glycine methyl ester

[0073]

[0074] The operation was the same as above to obtain 0.3016g of yellow powder, yield 70.44%, m.p.158 ~ 159°C. 1 H NMR (CDCl 3 , 400MHz), δ : 1.41 (s, 3H, CH 3 ), 2.44 (s, 3H, OCH 3 ), 4.39(d, J = 4.0 Hz, 2H, NHCH 2 ), 7.34-8.01 (m, 8H, 2×C 6 h 4 ).

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Abstract

The invention discloses a thiazol-aminobenzamide acetate derivative with anti-tumor activity. The thiazol-aminobenzamide acetate derivative with the anti-tumor activity can be applied to preparing anti-cancer drugs and is particularly applicable to serving as a Bcr-Abl tyrosine kinase inhibitor, especially as a Bcr-Abl tyrosine kinase inhibitor for T3151 mutation.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a series of thiazole aminobenzamide acetate derivatives, a preparation method and application thereof. Background technique [0002] Chronic myeloid leukemia (CML) is a malignant myeloproliferative disease originating from hematopoietic stem cells, accounting for 15%-20% of all leukemias, and is the most common myeloproliferative disease. The root cause of the disease is the Bcr-Abl gene formed by the fusion of the proto-oncogene c-Abl on chromosome 9 and the Bcr gene on chromosome 22. At present, it has been confirmed that Bcr-Abl tyrosine kinase is the most ideal molecular target for the treatment of CML (Blood, 1996, 87: 3036-3038; Blood, 2000, 96: 343-356). Around the Bcr-Abl tyrosine kinase, pharmaceutical workers have made various efforts. At present, the successfully marketed Bcr-Abl tyrosine kinase inhibitors include imatinib, nilotinib, radotinib, dasatinib, subotini...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/42A61P35/00A61P35/02A61K31/426
CPCA61P35/00A61P35/02C07D277/42
Inventor 彭俊梅刘娟黄红林曹轩刘映李娜柯栢怡李博
Owner NANHUA UNIV
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