55842-53-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Thiazolecarbonyl chloride, 2-methyl(9CI) is used as a versatile building block for the manufacturing of drugs to treat various diseases and ailments. Its reactivity and ability to form thiazole-containing compounds make it a valuable component in the development of new pharmaceuticals.
Used in Agrochemical Industry:
4-Thiazolecarbonyl chloride, 2-methyl(9CI) is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of products for agricultural applications.
Used in Organic Synthesis:
As a highly reactive reagent, 4-Thiazolecarbonyl chloride, 2-methyl(9CI) is utilized in organic synthesis, particularly in the preparation of thiazole-containing compounds for various applications.
Used in Dye and Pigment Production:
4-Thiazolecarbonyl chloride, 2-methyl(9CI) serves as a precursor in the production of dyes, pigments, and other fine chemicals, contributing to the creation of a wide range of colorants and specialty chemicals for various industries.

InChI:InChI=1/C5H4ClNOS/c1-3-7-4(2-9-3)5(6)8/h2H,1H3

Upstream product

• 35272-15-2 2-methylthiazole-4-carboxylic acid 

Downstream Products

• 1309778-73-1 N-{6-[5-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)-6-(methyloxy)-3-pyridinyl]-1H-indazol-4-yl}-2-methyl-1,3-thiazole-4-carboxamide 
• 1309778-78-6 2-methyl-N-[6-[3-(methylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide 
• 1309778-57-1 {[3-(4-{[(2-methyl-1,3-thiazol-4-yl)carbonyl]amino}-1H-indazol-6-yl)phenyl]oxy}acetic acid 
• 1309778-65-1 phenylmethyl [2-chloro-5-(4-{[(2-methyl-1,3-thiazol-4-yl)carbonyl]amino}-1H-indazol-6-yl)-3-pyridinyl]carbamate 
• 1309778-66-2 N-(6-{6-chloro-5-[fluoro(phenylsulfonyl)methyl]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 
• 1446442-98-3 2-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]thiazole-4-carboxamide 
• 1446442-67-6 5-iodo-2-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]thiazole-4-carboxamide 
• 1310556-85-4 2-methyl-N-(1-methyl-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-indazol-4-yl)-1,3-thiazole-4-carboxamide 
• 79690-79-2 2-bromo-1-(2'-methylthiazol-4'-yl)ethanone 
• 1173834-39-3 C₁₈H₂₁ClN₄OS 
• 1198437-75-0 2-methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide 
• 1309778-60-6 N-(6-{6-chloro-5-[methyl(phenylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 

Relevant academic research and scientific papers

Discovery of [1,2,4]triazolo[4,3-a]pyridines as potent Smoothened inhibitors targeting the Hedgehog pathway with improved antitumor activity in vivo

Triple-negative breast cancer (TNBC), a subset of breast cancers, have poorer survival than other breast cancer types. Recent studies have demonstrated that the abnormal Hedgehog (Hh) pathway is activated in TNBC and that these treatment-resistant cancers are sensitive to inhibition of the Hh pathway. Smoothened (Smo) protein is a vital constituent in Hh signaling and an attractive drug target. Vismodegib (VIS) is one of the most widely studied Smo inhibitors. But the clinical application of Smo inhibitors is limited to adult patients with BCC and AML, with many side effects. Therefore, it's necessary to develop novel Smo inhibitor with better profiles. Twenty [1,2,4]triazolo[4,3-a]pyridines were designed, synthesized and screened as Smo inhibitors. Four of these novel compounds showed directly bound to Smo protein with stronger binding affinity than VIS. The new compounds showed broad anti-proliferative activity against cancer cell lines in vitro, especially triple-negative breast cancer cells. Mechanistic studies demonstrated that TPB15 markedly induced cell cycle arrest and apoptosis in MDA-MB-468 cells. TPB15 blocked Smo translocation into the cilia and reduced Smo protein and mRNA expression. Furthermore, the expression of the downstream regulatory factor glioma-associated oncogene 1 (Gli1) was significantly inhibited. Finally, TPB15 demonstrated greater anti-tumor activity in our animal models than VIS with lower toxicity. Hence, these results support further optimization of this novel scaffold to develop improved Smo antagonists.

Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 μM) with no obvious cytotoxicity (CC50 > 50 μM). It effectively attenuated hypoxia-induced HIF-1α protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

Indazole derivatives for use in the treatment of influenza virus infection

The present invention is directed to compounds for use in the treatment or prevention of influenza virus infection.

Optimization of Novel Indazoles as Highly Potent and Selective Inhibitors of Phosphoinositide 3-Kinase δ for the Treatment of Respiratory Disease

Optimization of lead compound 1, through extensive use of structure-based design and a focus on PI3Kδ potency, isoform selectivity, and inhaled PK properties, led to the discovery of clinical candidates 2 (GSK2269557) and 3 (GSK2292767) for the treatment of respiratory indications via inhalation. Compounds 2 and 3 are both highly selective for PI3Kδ over the closely related isoforms and are active in a disease relevant brown Norway rat acute OVA model of Th2-driven lung inflammation.

Novel tetrahydropyrido[1,2-a]isoindolone derivatives (valmerins): Potent cyclin-dependent kinase/glycogen synthase kinase 3 inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number of diverse structures have been reported to inhibit CDKs and GSK-3β in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of our study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates for further development as anticancer agents.

NOVEL COMPOUNDS

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I): and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

INDAZOLE DERIVATIVES AS PI 3 - KINASE INHIBITORS

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I) and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

Pyrazolo[3,4-b]pyridine compounds, and their use as a PDE4 inhibitors

The invention provides a compound of formula (I) or a salt thereof: wherein R2 is H, C1-3alkyl, n-butyl, C1-2fluoroalkyl, cyclopropyl, cyclobutyl, (cyclopropyl)methyl-, —CN, or —CH2OH; R3 is inter alia optionally substituted C4-7cycloalkyl or an optionally substituted heterocyclic group (aa), (bb) or (cc); Ra is H, methyl or ethyl; Rb is H or methyl; R4 is H, methyl, ethyl, n-propyl, —C(O)-Me, or —C(O)—C1fluoroalkyl; and R5 is: —C(O)—(CH2)n—Ar, —C(O)-Het, —C(O)—C1-6alkyl, —C(O)—C1 fluoroalkyl, —C(O)—(CH2)2—C(O)—NR15bNR15b, —C(O)—CH2—C(O)—NR15bNR15b, —C(O)—NR15b—(CH2)m1—Ar, —C(O)—NR15b—Het, —C(O)—NR15b—C1-6alkyl, —C(O)—NR5aR5b, —S(O)2—(CH2)m2—Ar, —S(O)2-Het, —S(O)2—C1-6alkyl, or —CH2—Ar; or R4 and R5 taken together are —(CH2)p1—, —(CH2)2—X5—(CH2)2—, —C(O)—(CH2)p2—, —C(O)—N(R15)—(CH2)p3—; or NR4R5 is of sub-formula (y), (y1), (y2) or (y3). The invention provides the use of the compounds as inhibitors of phosphodiesterase type IV (PDE4) and/or for the treatment and/or prophylaxis of inflammatory and/or allergic diseases such as COPD and the like.

BENZPYRAZOL DERIVATIVES AS INHIBITORS OF PI3 KINASES

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I) and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

ION CHANNEL MODULATORS

The present teachings provide carboxylic amide compounds that can modulate the activity of ion channels in a mammal. The present teachings also provide processes for producing said compounds and their pharmaceutically acceptable salts, hydrates and esters, and methods of treating a pathological condition or disorder, or alleviating a symptom thereof, using said compounds including their pharmaceutically acceptable salts, hydrates and esters. The compounds can be useful in modulating ion channel activity including treating a variety of conditions associated with the abnormal modulation of one or more voltage-gated calcium channels.