98827-44-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-HYDROXY-2H-THIENO[2,3-E]-1,2-THIAZINE-3-CARBOXYLATE-1,1-DIOXIDE is used as a pharmaceutical intermediate for the development of novel therapeutic agents. Its unique molecular structure allows for the design of drugs with specific target interactions and potential applications in treating various diseases.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 4-HYDROXY-2H-THIENO[2,3-E]-1,2-THIAZINE-3-CARBOXYLATE-1,1-DIOXIDE is utilized as a precursor in the synthesis of new agrochemicals. Its properties may contribute to the creation of effective pesticides or herbicides with improved environmental profiles.
Used in Organic Synthesis:
METHYL 4-HYDROXY-2H-THIENO[2,3-E]-1,2-THIAZINE-3-CARBOXYLATE-1,1-DIOXIDE serves as a key building block in organic synthesis, enabling the construction of complex organic molecules with diverse applications in various industries, including pharmaceuticals, materials science, and specialty chemicals.
Used in Material Science:
In the field of material science, METHYL 4-HYDROXY-2H-THIENO[2,3-E]-1,2-THIAZINE-3-CARBOXYLATE-1,1-DIOXIDE is employed in the development of new materials with unique properties. Its incorporation into polymers or other materials may lead to advancements in areas such as electronics, sensors, or advanced materials with specific functionalities.

InChI:InChI=1/C8H7NO5S2/c1-14-8(11)5-6(10)7-4(2-3-15-7)16(12,13)9-5/h2-3,9-10H,1H3

Upstream product

• 106820-63-7 methyl 3-<<<(methoxcarbonyl)methyl>amino>sulfonyl>-2-thiophenecarboxylate 
• 59337-89-2 3-chlorothiophene-2-carboxylic acid 
• 59337-91-6 3-chlorosulfonyl-thiophene-2-carboxylic acid chloride 
• 59337-92-7 2-(carbomethoxy)thiophene-3-sulfonyl chloride 
• 59337-94-9 2,3-dihydro-3-oxo-thieno<2,3-d>isothiazole-1,1-dioxide 
• 1028285-17-7 (1,1,3-Trioxo-1,3-dihydro-1λ⁶-thieno[2,3-d]isothiazol-2-yl)-acetic acid methyl ester 

Downstream Products

• 59804-37-4 tenoxicam 
• 59804-25-0 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide 
• 106820-69-3 4-Hydroxy-2-(4-methoxy-benzyl)-1,1-dioxo-1,2-dihydro-1λ⁶-thieno[2,3-e][1,2]thiazine-3-carboxylic acid pyridin-2-ylamide 
• 59804-42-1 N-(3-chlorophenyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 59804-40-9 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 4-hydroxy-anilide 
• 59804-41-0 4-hydroxy-N-(3-methylphenyl)-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 59804-36-3 4-hydroxy-2-methyl-N-phenyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 106820-61-5 methyl 4-hydroxy-2-<(4-methoxyphenyl)methyl>-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide 

Relevant academic research and scientific papers

5-aminothiazole non-steroidal anti-inflammatory compound as well as preparation method and application thereof

The invention discloses a 5-aminothiazole non-steroidal anti-inflammatory compound. The compound which is efficient, low in toxicity and small in side effect is prepared from an ester intermediate containing a thiazine ring and a 5-aminothiazole derivative through a transesterification reaction. The preparation method of the compound is simple, the compound has the active groups of the existing non-steroidal anti-inflammatory medicine; meanwhile, the special change of the nitrogen atom position is also designed; compared with the existing non-steroidal anti-inflammatory medicines, the compoundhas better anti-inflammatory and analgesic effects, particularly has good curative effects on arthritis, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, soft tissue inflammation and thelike, has small toxic and side effects on human bodies, and has a very wide market prospect.

Preparation method of tenoxicam

The invention discloses a preparation method of tenoxicam and belongs to the technical field of medicine preparation. The preparation method comprises the following steps: using 3-chlorosulfonyl-2-thiophenecarboxylate, namely TNXK-0 as a raw material to synthesize 3-((N-(methoxycarbonyl) methyl) sulfonyl)-2-thiophenecarboxylate, namely TNXK-1; using the TNXK-1 as a raw material to synthesize 4-hydroxy-2H-thieno (2,3e)-1,2-thiazine-3-methyl formate-1,1-dioxide, namely TNXK-2; using the TNXK-2 as a raw material to synthesize 4-hydroxy-2-methyl-2H-thieno (2,3e)-1,2-thiazine-3-methyl formate-1,1-dioxide, namely TNXK-3; using the TNXK-3 and 2-aminopyridine as raw materials to synthesize the tenoxicam. The preparation method of the tenoxicam, disclosed by the invention, has the advantages of simple process, high yield and low cost; the purity of an obtained product is high.

Synthesis method of tenoxicam

The invention relates to a synthesis method of tenoxicam. The synthesis method takes 3-[[N-(methoxycarbonyl)methyl]sulfonyl]-2-thiophenecarboxylate as a starting raw material and comprises the following steps: carrying out cyclization on the starting raw material to obtain a 4-hydroxy-2H-thieno[2,3-e]-1,2-thiazine-3-methyl formate1,1-dioxide intermediate; carrying out reaction on the 4-hydroxy-2H-thieno[2,3-e]-1,2-thiazine-3-methyl formate1,1-dioxide intermediate, dimethyl carbonate and 2-aminopyridine through a one-pot method to prepare the tenoxicam. A synthesis route is as follows: the synthesis route is shown in the description. The synthesis method provided by the invention has the advantages that the synthesis method has a short route and no hazardous process and is green and environmentally friendly; a final aminolysis step is avoided and raw materials react completely; the yield is more than or equal to 80 percent; the raw materials and a product are not easy to carbonize and decompose and side reaction is reduced; the product is easy to purify and the purity of the product can reach 99.85 percent; the synthesis method is a synthesis process capable of realizing industrialized production.

Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity

Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3- carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4- dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.

Analogues and Derivatives of Tenoxicam. 1. Synthesis and Antiinflammatory Activity of Analogues with Different Residues on the Ring Nitrogen and the Amide Nitrogen

The synthesis of tenoxicam, 4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno-1,2-thiazine-3-carboxamide 1,1-dioxide (1e), and of the analogues with various residues on the ring nitrogen and the amide nitrogen is described.This new class of "oxicams" has pronounced antiinflammatory and analgesic properties.The very specific structure-activity relationship of isomeric and isosteric groups at the amide nitrogen has been evaluated.The substituent in position 2 also has a great influence on the pharmacological properties.Tenoxicam is presently underrgoing clinical trials.