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Xanthine derivative

A compound, pharmaceutical technology, applied in the field of dipeptidyl peptidase IV inhibitor

Active Publication Date: 2014-01-15
CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the many side effects of these hypoglycemic drugs, it is particularly important to develop a new type of drug with low side effects and effective treatment of diabetes.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3 Preparation of -amino-piperidin-1-yl]-xanthine

[0032]

[0033] Preparation of the first step 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

[0034] Using known methods, 8-bromo-3-methylxanthine (5g, 20.4mmol) was dissolved in N,N-dimethylformamide (30ml), N,N diisopropylethylamine (2.633 g, 20.4mmol), 1-bromo-2-butyne (2.714g, 20.4mmol), react overnight at room temperature, follow the reaction process by thin-layer chromatography, after the reaction is complete, pour the reaction solution into water, filter with suction, and wash the solid with water for 3 times and dried to obtain 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (5.15 g, light yellow solid), yield: 85%.

[0035] MS m / z(ES):297,299[M+1]

[0036] The second step 1-[(5-fluoro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-yellow Preparation of purine

[0037] 3-Methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (15...

Embodiment 2

[0047] 1-[(1,3-Benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-amino-piper Preparation of pyridin-1-yl]-xanthine

[0048]

[0049]

[0050] The first step is the same as the first step in implementation example 1;

[0051] The second step is the preparation of 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine

[0052] 3-Methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (327mg, 1mmol) was dissolved in N,N-dimethylformamide (5ml) by a known method Add potassium carbonate (221mg, 1.6mmol), 2-bromomethyl-1,3-benzothiazole (228mg, 1mmol), react overnight at room temperature, track the reaction progress by thin-layer chromatography, after the reaction is complete, pour the reaction solution into water, filtered with suction, washed the solid with water, and dried to obtain 1-[(1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)- 8-Bromo-xanthine 2b (400 mg, yellow solid), yield: 90%.

[0053] MS m / z(ES):444,446[M+1]

[0054] The third...

Embodiment 3

[0062] 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3 Preparation of -amino-piperidin-1-yl]-xanthine

[0063]

[0064] The first step is the same as the first step in implementation example 1;

[0065] The second step 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromo-yellow Preparation of purine

[0066] Using a known method, 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (297mg, 1mmol) was dissolved in N,N-dimethylformamide (8ml) , add 2-bromomethyl-5-chloro-1,3-benzothiazole (263mg, 1mmol), potassium carbonate (213mg, 1.5mmol), react at room temperature overnight, after TLC tracking the reaction is complete, pour into water , filtered with suction, washed with water, and dried to give 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl) -8-Bromo-xanthine 3b (460 mg, pale yellow solid), yield: 96%.

[0067] MS m / z(ES):478,480[M+1]

[0068] The third step 1-[(5-chloro-1,3-benzothiazol-2-yl)methyl...

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Abstract

The invention discloses a xanthine derivative and its pharmaceutically acceptable salt. In vitro DPP-IV activity inhibition tests, influence tests of normal mouse's glucose tolerance, and influence tests of spontaneous diabetic mouse's blood glucose confirm that the compound and its pharmaceutically acceptable salt show significant DPP-IV inhibitory activity, and can be used in preparation of drugs for treating dipeptidyl peptidase IV associated diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of xanthine derivatives, a preparation method and the use of the derivatives as therapeutic drugs, especially dipeptidyl peptidase IV (DPP-IV) inhibitors. Background technique [0002] Diabetes mellitus is a metabolic disease of multiple etiologies characterized by chronic hyperglycemia accompanied by disturbances in carbohydrate, fat and protein metabolism due to defects in insulin secretion and / or action. Diabetes is also a very old disease, which is due to the relative or absolute lack of insulin in the human body, which causes the blood glucose concentration to rise, resulting in a large amount of sugar being excreted from the urine, accompanied by polydipsia, polyuria, polyphagia, weight loss, and dizziness , fatigue and other symptoms. [0003] In diabetes treatment, exercise therapy and diet therapy are two essential diabetes treatment methods. When these two t...

Claims

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Application Information

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IPC IPC(8): C07D473/04A61K31/522A61P3/10
CPCC07D473/04A61K31/437A61K31/522C07D473/06A61P43/00A61P3/10C07D473/08
Inventor 王颖向永哲岑国栋黄龙刘建周宁张济兵
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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