17969-20-9

Usage

Uses

Used in Pharmaceutical Industry:
2-[2-(4-CHLOROPHENYL)-1,3-THIAZOL-4-YL]ACETIC ACID is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain and fever. However, its use is limited due to its hepatotoxic nature, and caution must be exercised when administering 2-[2-(4-CHLOROPHENYL)-1,3-THIAZOL-4-YL]ACETIC ACID to patients.

Originator

Fenclozic Acid,ZYF Pharm Chemical

Manufacturing Process

3.7 parts of 2-(4-chlorophenyl)-4-cyanomethylthiazole and 35 parts of 6 N hydrochloric acid are heated under reflux for 2 hours. The solution is cooled by the addition of ice and made alkaline to pH 8 by the addition of 30% aqueous ammonia. The mixture is filtered to remove trace impurities, and an excess of 40% sodium hydroxide solution is then added to the filtrate to cause precipitation of a sodium salt, which is collected by filtration and crystallised from water. There is thus obtained sodium 2-(4-chlorophenyl)thiazol-4- ylacetate, M.P. 13°C (decomposition).This sodium salt is dissolved in hot water, and the solution is brought to pH 4 by the addition of acetic acid, which causes the precipitation of 2-(4- chlorophenyl)thiazol-4-ylacetic acid. This is collected by filtration, washed with water, and dried in vacuo over phosphorus pentoxide. It has an M.P. 155- 156°C (from ethyl acetate).

Therapeutic Function

Antiinflammatory, Analgesic, Antipyretic

InChI:InChI=1/C11H8ClNO2S/c12-8-3-1-7(2-4-8)11-13-9(6-16-11)5-10(14)15/h1-4,6H,5H2,(H,14,15)/p-1

Upstream product

• 27473-03-6 2-(2-(4-chlorophenyl)thiazol-4-yl)ethan-1-ol 

Downstream Products

• 17969-62-9 N-{[2-(4-chloro-phenyl)-thiazol-4-yl]-acetyl}-glycine methyl ester 
• 1443534-18-6 (2S,3S,4S,5R,6S)-benzyl 6-({2-[2-(4-chlorophenyl)[2-¹⁴C]-1,3-thiazol-4-yl]acetyl}oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 
• 27473-03-6 2-(2-(4-chlorophenyl)thiazol-4-yl)ethan-1-ol 
• 40361-47-5 1-[2-(4-chloro-phenyl)-thiazol-4-yl]-ethane-1,2-diol 
• 40361-75-9 [2-(4-chloro-phenyl)-4,5-dihydro-thiazol-4-yl]-methanol 
• 17969-36-7 2-[2-(4-chloro-phenyl)-thiazol-4-yl]-acetamide 
• 40361-49-7 N-{[2-(4-chloro-phenyl)-thiazol-4-yl]-acetyl}-alanine methyl ester 
• 40361-50-0 N-{[2-(4-chloro-phenyl)-thiazol-4-yl]-acetyl}-serine methyl ester 
• 40361-65-7 2-[2-(4-chloro-phenyl)-thiazol-4-yl]-N-cyclohexyl-N-cyclohexylcarbamoyl-acetamide 

Relevant academic research and scientific papers

Prodrugs of non-steroidal anti-inflammatory and carboxylic acid containing compounds

Compounds of the formula: RC(O)O-spacer-OC(O)R′, wherein (i) RC(O)— is the acyl residue of an NSAID or other pharmaceutically active agent bearing a carboxylic acid function, (ii) spacer is Cn alkyl, (iii) n is from 1 to 6, and (iv) R′ is substituted or unsubstituted heteroaryl or heterocycle, and pharmaceutical compositions thereof.