54237-09-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Thiazolecarbonyl chloride, 4-methyl(9CI) is used as a key intermediate for the synthesis of active pharmaceutical ingredients. Its reactivity allows for the creation of various thiazole-based compounds, which are often found in drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Thiazolecarbonyl chloride, 4-methyl(9CI) serves as a precursor in the production of crop protection chemicals. Its ability to form thiazole derivatives makes it valuable for developing new pesticides and other agrochemicals that protect crops from pests and diseases.
Used in Research and Development:
5-Thiazolecarbonyl chloride, 4-methyl(9CI) is also utilized in research and development for the production of new chemical entities with biological activity. Its potential use in creating novel compounds makes it a valuable tool for scientists working on the discovery and development of new pharmaceuticals and agrochemicals.

Upstream product

• 20485-41-0 4-methylthiazole-5-carboxylic acid 

Downstream Products

• 69973-66-6 (4-methyl-thiazol-5-yl)-phenyl-methanone 
• 70002-61-8 (4-methoxy-phenyl)-(4-methyl-thiazol-5-yl)-methanone 
• 103985-97-3 1-(4-methyl-5-thiazolyl)-1-phenylmethanol 
• 82294-70-0 4-methyl-1,3-thiazole-5-carbaldehyde 
• 953071-40-4 1-(3-chlorophenyl)-3-(4-methylthiazol-5-yl)propane-1,3-dione 
• 1050203-49-0 N-((1-chloro-8-fluoroisoquinolin-4-yl)methyl)-N-(3-chlorophenyl)-4-methylthiazole-5-carboxamide 
• 1108707-44-3 N-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methyl)-N,4-dimethylthiazole-5-carboxamide 
• 953068-15-0 4-((3-(3-chlorophenyl)-5-(4-methylthiazol-5-yl)-1H-pyrazol-4-yl)methyl)-8-fluoroquinolin-2(1H)-one 
• 81569-44-0 methyl 4-methyl thiazole-5-carboxylate 
• 1155194-71-0 N-(3-chlorophenyl)-4-methyl-N-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)thiazole-5-carboxamide 
• 1050203-16-1 N-(3-chlorophenyl)-N-((8-fluoroisoquinolin-4-yl)methyl)-4-methylthiazole-5-carboxamide 
• 1155194-67-4 N-(3-chlorophenyl)-N-((8-fluoroquinolin-4-yl)methyl)-4-methylthiazole-5-carboxamide 
• 1155194-62-9 N-(3-chlorophenyl)-N-((8-fluoro-2-oxo-2H-chromen-4-yl)methyl)-5-methylthiazole-4-carboxamide 
• 1155195-26-8 N-((2-chloro-5,6,7,8-tetrahydroquinolin-4-yl)methyl)-N-(3-chlorophenyl)-4-methylthiazole-5-carboxamide 

Relevant academic research and scientific papers

Efficient and eco-friendly preparation of 4-methyl-5-formyl-thiazole

4-Methyl-5-formylthiazole, an intermediate for synthesizing cefditoren pivoxil, was prepared in good yield by Pd/BaSO4 catalyzed hydrogenation of 4-methylthiazole-5-carboxylic acid chloride. Detailed reaction conditions have been studied.

Enantioselective Allylic Substitution of Morita-Baylis-Hillman Adducts Catalyzed by Chiral Bifunctional Ferrocenylphosphines

A series of air-stable chiral ferrocenylphosphines (LB1-LB4) were prepared and used in the asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) adducts with phthalimide under mild reaction conditions; the (R,SFc)-ferrocenylphosphine LB4 afforded the desired amination products 3 in moderate yields with excellent enantioselectivities. The absolute configuration of 3o was confirmed by X-ray analysis.

Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines

A series of N-substituted tetrahydro-β-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 μM, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 μM, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L. donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 μM. Several analogs also displayed antitrypanosomal activity against Trypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 μM, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages).

ANTIBACTERIAL AMIDE AND SULFONAMIDE SUBSTITUTED HETEROCYCLIC UREA COMPOUNDS

The present invention provides novel amide and sulfonamide substituted heterocyclic urea compounds having useful antibacterial activity. Use of these compounds as pharmaceutical compositions and method of their production are also provided.

Discovery of inducible nitric oxide synthase (iNOS) inhibitor development candidate KD7332, part 1: Identification of a novel, potent, and selective series of quinolinone iNOS dimerization inhibitors that are orally active in rodent pain models

There are three isoforms of dimeric nitric oxide synthases (NOS) that convert arginine to citrulline and nitric oxide. Inducible NOS is implicated in numerous inflammatory diseases and, more recently, in neuropathic pain states. The majority of existing NOS inhibitors are either based on the structure of arginine or are substrate competitive. We describe the identification from an ultra high-throughput screen of a novel series of quinolinone small molecule, nonarginine iNOS dimerization inhibitors. SAR studies on the screening hit, coupled with an in vivo lipopolysaccharide (LPS) challenge assay measuring plasma nitrates and drug levels, rapidly led to the identification of compounds 12 and 42 - potent inhibitors of the human and mouse iNOS enzyme that were highly selective over endothelial NOS (eNOS). Following oral dosing, compounds 12 and 42 gave a statistical reduction in pain behaviors in the mouse formalin model, while 12 also statistically reduced neuropathic pain behaviors in the chronic constriction injury (Bennett) model.

QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS

The present invention relates to novel quinolones of Formula I that inhibit inducible NOS synthase together with methods of synthesizing and using the compounds including methods for inhibiting or modulating nitric oxide synthesis and/or lowering nitric oxide levels in a patient by administering the compounds for the treatment of disease.

Benzoxazole carboxamides for treating CINV and IBS-D

Compounds of formulae I and II: are disclosed as 5-HT3 inhibitors. Those compounds that exhibit central activity are useful in treating CINV; those that inhibit peripheral receptors are useful to treat IBS-D.

Process for the preparation of thiazolecarboxylic acid chlorides

Disclosed herein is a process for the preparation of a thiazolecarboxylic acid chloride represented by the following general formula (II): STR1 wherein R1 represents a hydrogen or halogen atom, a lower alkyl group, a lower alkoxy group, or a lower alkyl group substituted by a halogen atom or lower alkoxy group, and R2 represents a hydrogen atom, a lower alkyl group, or a lower alkyl group substituted by a halogen atom or lower alkoxy group, which comprises reacting a thiazolecarboxylic acid represented by the following general formula (I): STR2 wherein R1 and R2 have the same meanings as defined with respect to formula (II), with phosgene or trichloromethyl chloroformate in the presence or absence of a catalyst.