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2-((2-(3-aminopiperidine-1)-4-oxythiophene (3, 2-d) pyrimidine-3(4H)-methyl) polymorphic benzonitrile, and preparation method and pharmacological applications thereof

A technology of aminopiperidine and oxythiophene, which is used in drug combinations, active ingredients of heterocyclic compounds, metabolic diseases, etc.

Inactive Publication Date: 2012-09-12
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So the study of DPP4 inhibitors is still a big challenge

Method used

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  • 2-((2-(3-aminopiperidine-1)-4-oxythiophene (3, 2-d) pyrimidine-3(4H)-methyl) polymorphic benzonitrile, and preparation method and pharmacological applications thereof
  • 2-((2-(3-aminopiperidine-1)-4-oxythiophene (3, 2-d) pyrimidine-3(4H)-methyl) polymorphic benzonitrile, and preparation method and pharmacological applications thereof
  • 2-((2-(3-aminopiperidine-1)-4-oxythiophene (3, 2-d) pyrimidine-3(4H)-methyl) polymorphic benzonitrile, and preparation method and pharmacological applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: Preparation of Form A of 2-((2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile

[0063] Dissolve 200 mg of 2-((2-(3-aminopiperidine-1)-4-oxothieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile in 1 mL of ethyl acetate , add 3mL of petroleum ether, crystallize under stirring at room temperature, until no solid precipitates out, filter, place the obtained solid material in a vacuum drying oven, and vacuum dry for 70 hours at 25°C and 5KPa to obtain 2-(( 100 mg of 2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile A crystal.

Embodiment 2

[0064] Example 2: Preparation of Form A of 2-((2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile

[0065] Dissolve 200 mg of 2-((2-(3-aminopiperidine-1)-4-oxothiophene[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile in 1 mL of ethanol, add 12mL of petroleum ether was crystallized under stirring at room temperature until no solid precipitated out, filtered, and the obtained solid material was placed in a vacuum drying oven, and vacuum-dried at 25°C and 5KPa for 70 hours to obtain 2-((2- (3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile A crystal 110 mg.

Embodiment 3

[0066] Example 3: Preparation of Form A of 2-((2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile

[0067]Dissolve 200 mg of 2-((2-(3-aminopiperidine-1)-4-oxothieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile in 1 mL of ethyl acetate , add 12mL of n-heptane, crystallize under stirring at room temperature, until no solid precipitates out, filter, place the resulting solid material in a vacuum drying oven, and vacuum dry for 70 hours at 25°C and 5KPa to obtain 2-( (2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methyl)benzonitrile A crystal 100 mg.

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Abstract

The invention discloses 2-((2-(3-aminopiperidine-1)-4-oxythiophene (3, 2-d) pyrimidine-3(4H)-methyl) polymorphic benzonitrile, and a preparation method and pharmacological applications thereof. Compared with the prior art, the polymorphic benzonitrile has the advantages of high DPP4 (dipeptidyl peptidase-4) inhibitory activity, high in-vivo sugar reducing activity and fine pharmacokinetic characteristics, and is especially suitable for treatment of type 2 diabetes mellitus.

Description

technical field [0001] The present invention relates to crystals of pharmaceutical compounds, in particular, the present invention relates to 2-((2-(3-aminopiperidine-1)-4-oxythieno[3,2-d]pyrimidine-3(4H)-methanol Base) benzonitrile polymorph, its preparation method, crystal composition, pharmaceutical composition and use. Background technique [0002] Diabetes is a common metabolic disease. It is characterized by abnormally high plasma glucose concentrations and hyperglycemia in the fasted state or following an oral glucose tolerance test. The World Health Organization divides diabetes into type 1 and type 2 according to the clinical form, and most diabetic patients have type 2 diabetes mellitus (T2DM). Type 2 diabetes, also known as non-insulin-dependent diabetes, has a high risk of vascular complications, such as coronary artery disease, stroke, hypertension, nephropathy, peripheral vascular disease, neurological disease, and retinopathy. This metabolic disease has bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/522A61P3/10
Inventor 柳红李佳王江李静雅李建周圣斌苏明波蒋华良罗小民陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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