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Amide thiazole derivant, preparation method and use thereof

一种乙酰基、烷基的技术，应用在糖尿病相关的药物领域，能够解决未发现体重增加等问题

Inactive Publication Date: 2009-06-03
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinical results show that this type of drug has a good hypoglycemic effect, and no adverse reactions such as weight gain and hypoglycemia, which are common in other diabetes drugs, have been found

Method used

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  • Amide thiazole derivant, preparation method and use thereof
  • Amide thiazole derivant, preparation method and use thereof
  • Amide thiazole derivant, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 2-(2-Chloroacetyl)amino-4-methylthiazole (III-1)

[0037]

[0038] In a 100mL round bottom flask, add 1.14g (10mmol) compound II-1, 1.31g (13mmol) dry triethylamine and 50mL dry CH 2 Cl 2 , the mixture was cooled with an ice-water bath under stirring, and then slowly added dropwise 1.24 g (11 mmol) of chloroacetyl chloride dissolved in 5 mL of dry CH 2 Cl 2 After the resulting solution was added dropwise, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with 50 mL CH 2 Cl 2 After dilution, it was washed with saturated brine, and the organic phase was washed with anhydrous Na 2 SO 4After drying, the solvent was removed on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain the pure product of compound III-1, 1.75 g, with a yield of 92%. Colorless crystals, melting point 128-129°C, IR (KBr), 3185, 3053, 1653, 1578, 1380cm -1 .

[0039] Compounds II-1 and III-1 are one of ...

Embodiment 2-5

[0041] With the operation of Example 1, replace the compound II-1 in Example 1 with the compound II-2 to II-5 in the following table, and some examples use organic base diisopropylethylamine or 4-dimethylamine Basepyridine instead of triethylamine in Example 1, all the other operations are the same as in Example 1 to obtain compounds III-2 to III-5 listed in the table below.

[0042] Compounds II-2 to II-5 and compounds III-2 to III-5 belong to two classes of compounds having the general formula II and having the general formula III, respectively.

[0043] implement

Sequence

No

Yield

(%)

organic base

II

III

2

92

Diisopropyl

Ethylamine II-2: 2-Amino

Thiazole

III-2: 2-(2-Chloroacetyl)aminothiazole

3

90

4-Dimethylamino

pyridine II-3: 2-Amino

-4-Bromothiazole

III-3: 4-Bromo-2-(2-chloroacetyl)aminothiazole

4

...

Embodiment 6

[0054] 4-Bromo-2-{2-[(2-chlorobenzyl)amino]acetyl}aminothiazole (I-1)

[0055]

[0056] Add 1.77g (10mmol) compound III-2, 1.61g (15mmol) benzylamine (IV-1) and 1.01g (10mmol) triethylamine to a 100mL round bottom flask, then add 25mL dry THF to dissolve. The resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated to remove the solvent on a rotary evaporator to obtain a crude product of compound I-1, which was purified by column chromatography to obtain a pure product of compound I-1. Colorless oil, 2.22g, yield 90%. IR(KBr), 3237, 3186, 3030, 1654cm -1 .

[0057] Compounds IV-1 and I-1 are one of the compounds having the general formula IV and the general formula I, respectively.

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PUM

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Abstract

The invention relates to drug filed relative to diabetes, in particular dipeptidyl peptidase-IV inhibitor having amide thiazole structure with general formula I medicative to diabetes, preparation method thereof, drug composition containing the same and application in preparing diabetes drug. Wherein the radical is defined as the specification.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a dipeptidyl peptidase-IV inhibitor containing an amidothiazole structure, a preparation method thereof, and a pharmaceutical composition containing the same for diabetes. Background technique [0002] According to statistics, there are about 170 million diabetic patients in the world at present, and about 90% of them are type II (ie, non-insulin-dependent) diabetic patients. At present, the antidiabetic drugs in clinical use mainly include metformin, sulfonylureas and insulin drugs. In recent years, thiazolidinedione drugs and α-glucosidase inhibitors have also been listed on the market. These drugs have good therapeutic effects, but there are safety problems in long-term treatment, such as liver toxicity and weight gain. [0003] Dipeptidyl peptidase IV (dipeptidyl peptidase IV, DPP-IV) can efficiently and rapidly degrade glucagon-like...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/46C07D277/56C07D417/12A61K31/426A61K31/427A61P3/10
CPCC07D277/46C07D277/58C07D417/12A61P3/10
Inventor 赵桂龙徐为人李祎亮邹美香战付旭王玉丽刘巍张士俊汤立达王建武
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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