Heterocyclic compound and application thereof

A technology of heterocyclic compounds and heteroaryl groups, applied in the field of medicinal chemistry, can solve problems such as poor activity

Pending Publication Date: 2021-02-02
SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compounds with the above structures have poor activity as agonists. Therefore, based on this background, it is necessary to develop novel thyroid hormone mimics with good agonist activity, TRβ selectivity and liver selectivity.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Heterocyclic compound and application thereof
  • Heterocyclic compound and application thereof
  • Heterocyclic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0049] The present invention has no special requirements on the preparation method of the aforementioned heterocyclic compound, and those skilled in the art can select a suitable preparation process based on the target product based on the general knowledge of synthesis. Can be synthesized as follows:

[0050]

[0051] Including but not limited to the following specific preparation process:

[0052]

[0053] a. Alkali (potassium carbonate, cesium carbonate, sodium carbonate, etc.), cuprous iodide, N,N-dimethylformamide

[0054] b. Ethyl acrylate, trifluoroacetic acid c. Sodium hydroxide, water, methanol

[0055] d. Ethyl chloroformylacetate, N,N-diisopropylethylamine, tetrahydrofuran e. Sodium hydroxide, water, methanol

[0056] f. Hydrochloric acid, sodium nitrite, N-cyanoacetylurethane, water, pyridine g. Acetic acid, sodium acetate.

[0057] The present invention also provides an application of the heterocyclic compound described in the present invention in the pre...

Embodiment 1

[0073] 2-(3,5-Dichloro-4-((7-methyl-7H-pyrrole[2,3-d]pyrimidin-4-yl)oxy)-phenyl)-3,5-dioxo -2,3,4,5-Tetrahydro-[1,2,4]triazine-6-carbonitrile

[0074]

[0075] Step 1: Preparation of 2,6-dichloro-4-aminophenol

[0076] 2,6-Dichloro-4-nitrophenol (4.2g, 0.02mol) was dissolved in ethanol (20ml) and water (4ml), and acetic acid (2ml) was added. Then heat and stir to raise the temperature to 90° C., and add Fe powder (5.6 g, 0.1 mmol) in batches. After the addition, the reaction solution was kept warm for 30 minutes, then the heating was stopped, and it was filtered while it was hot. The product was finally separated by column chromatography (ethyl acetate / petroleum ether=1 / 3). 2,6-Dichloro-4aminophenol (3.35 g, 94.1% yield) was obtained.

[0077] LC-MS (m / z) 177.2 (M-1).

[0078] Step 2: Preparation of 4-chloro-7-methyl--7H-pyrrolo[2,3-d]pyrimidine

[0079] Dissolve 4-chloro-7H-pyrrole[2,3-d]pyrimidine (615mg, 4mmol) in tetrahydrofuran (10ml), under nitrogen protection, ...

Embodiment 2

[0092] 3-((3,5-dichloro-4-((7-methyl-7H-pyrrole[2,3-d]pyrimidin-4-yl)oxy)-phenyl)-amino)-3-oxo propionic acid

[0093]

[0094]Step 1: Preparation of 3-((3,5-dichloro-4-((7-methyl-7H-pyrrole[2,3-d]pyrimidin-4-yl)oxy)-phenyl)-amino) -Ethyl 3-oxopropionate

[0095] 3,5-Dichloro-4-((7-methyl-7H-pyrrole[2,3-d]pyrimidin-4-yl)oxy)aniline (62mg, 0.2mmol) was dissolved in tetrahydrofuran (3ml) , and N,N-diisopropylethylamine (65 mg, 0.5 mmol) was added. Then the temperature was lowered to 0-5°C, and ethyl chloroformoacetate (45mg, 0.3mmol) was added. After the addition was complete, the mixture was raised to room temperature and stirred for 2 hours. After the reaction of the raw materials was complete, water was added, followed by ethyl acetate for extraction, the combined organic phases were dried, filtered, and evaporated under reduced pressure to obtain a residue, which was finally separated by column chromatography (ethyl acetate / petroleum ether=1 / 2). 3-((3,5-Dichloro-4-((...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a heterocyclic compound with a structure as shown in a formula (I) which is described in the specification, and experimental results show that the heterocyclic compound providedby the invention has good activity as a thyroid hormone beta receptor stimulant and can be used for treating and/or preventing diseases caused by thyroid hormone regulation.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on July 31, 2019, the application number is 201910702174.5, and the title of the invention is "a heterocyclic compound and its application", the entire content of which is incorporated by reference in this application middle. technical field [0002] The invention relates to the technical field of medicinal chemistry, in particular to a heterocyclic compound and its application. Background technique [0003] Thyroid hormone (TH) plays a key role in normal growth and development and maintenance of metabolic balance (Paul MYen, Physiological Reviews, Vol. 81(3): pp. 1097-1126 (2001)). TH can promote the hydrolysis of lipids, increase the utilization of fatty acids, thereby providing energy for the body, and finally lead to the reduction of lipids and weight loss. Studies have shown that the TH level of obese patients has a great change compared with that of norma...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D403/04C07D239/47C07D487/04C07D213/81C07D403/14A61P5/14A61P3/04A61P3/06A61P3/10A61P1/16A61P9/10A61P9/00A61P35/00A61K31/53A61K31/505A61K31/506A61K31/519A61K31/44
CPCA61P1/16A61P3/04A61P3/06A61P3/10A61P5/14A61P9/00A61P9/10A61P35/00C07D213/81C07D239/47C07D403/04C07D403/12C07D403/14C07D487/04A61K31/44A61K31/4427A61K31/505A61K31/506A61K31/519A61K31/53C07D213/16C07D239/48C07D239/50
Inventor 邓舟王伟周游鲁先平李志斌
Owner SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap