194086-61-8

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide is used as a chemical intermediate for the preparation of fused 1,2,4-thiadiazines. These fused 1,2,4-thiadiazines are important in the development of compounds that act as openers of the KATP-regulated potassium channels. The opening of these channels can have therapeutic applications in various conditions, such as hypertension and certain types of heart diseases.
Used in Chemical Synthesis:
As a colorless solid with unique chemical properties, 3,6-Dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide can be utilized in various chemical synthesis processes. Its reactivity and structural features make it a valuable building block for the creation of novel compounds with potential applications in different industries, such as pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 7440-44-0 pyrographite 
• 194086-60-7 6-chloro-2,3-dihydro-3-oxo-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 

Downstream Products

• 319002-53-4 3-amino-6-chloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 
• 279215-43-9 6-chloro-3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide 

Relevant academic research and scientific papers

6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic β-cells

6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives were synthesized and characterized as activators of adenosine 5′-triphosphate (ATP) sensitive potassium (KATP) channels in the β-cells by measuring effects on membrane potential and insulin release in vitro. The effects on vascular tissue in vitro were measured on rat aorta and small mesenteric vessels. Selected compounds were characterized as competitive inhibitors of [3H]glibenclamide binding to membranes of HEK293 cells expressing human SUR1/Kir6.2 and as potent inhibitors of insulin release in isolated rat islets. 6-Chloro-3-(1-methylcyclobutyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (54) was found to bind and activate the SUR1/Kir6.2 KATP channels in the low nanomolar range and to be at least 1000 times more potent than the reference compound diazoxide with respect to inhibition of insulin release from rat islets. Several compounds, e.g., 3-propylamino- (30), 3-isopropylamino- (34), 3-(S)-sec-butylamino- (37), and 3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (53), which were found to be potent and β-cell selective activators of KATP channels in vitro, were found to inhibit insulin secretion in rats with minimal effects on blood pressure and to exhibit good oral pharmacokinetic properties.

Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use

1,2,4-Thiadiazine and 1,4-thiazine derivatives represented by the formula STR1 wherein A, B, D, R1, R2, R3 and R4 are defined in the description, compositions thereof and methods for preparing the compounds are described. The compounds are useful in the treatment of diseases of the central nervous system, the cardiovascular system, the pulmonary system, the gastrointestinal system and the endocrinologic system.