28466-21-9

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-1,3,5-TRIMETHYLPYRAZOLE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity enable the development of new drugs with improved therapeutic properties and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical sector, 4-AMINO-1,3,5-TRIMETHYLPYRAZOLE serves as a crucial building block for the synthesis of novel agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection, contributing to sustainable agriculture.
Used in Material Science:
4-AMINO-1,3,5-TRIMETHYLPYRAZOLE is utilized in the development of new materials due to its high stability and reactivity. Its unique chemical properties allow for the creation of innovative materials with improved performance characteristics, such as enhanced durability, thermal stability, and chemical resistance.
Used in Chemical Process Development:
4-AMINO-1,3,5-TRIMETHYLPYRAZOLE's reactivity and stability make it a valuable asset in the development of new chemical processes. 4-AMINO-1,3,5-TRIMETHYLPYRAZOLE can be employed as a catalyst or reactant in various chemical reactions, leading to the production of new compounds with diverse applications across different industries.

InChI:InChI=1/C6H11N3/c1-4-6(7)5(2)9(3)8-4/h7H2,1-3H3

Upstream product

• 1125-30-0 1,3,5-trimethyl-4-nitro-1H-pyrazole 
• 7171-70-2 1,3,5-trimethyl-4-nitrosopyrazole 
• 29917-12-2 Isonitrosoacetylacetone 
• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 14531-55-6 3,5-dimethyl-4-nitro-1H-pyrazole 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 15801-69-1 4-bromo-1,3,5-trimethylpyrazole 

Downstream Products

• 100373-74-8 benzylidene-(1,3,5-trimethyl-1H-pyrazol-4-yl)-amine 
• 107203-65-6 (4-dimethylamino-benzylidene)-(1,3,5-trimethyl-1H-pyrazol-4-yl)-amine 
• 221089-38-9 1-(2-chloro-6-methyl-phenyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea 
• 221089-31-2 1-(5-chloro-2-methyl-phenyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea 
• 221089-39-0 1-(4-chloro-2-methyl-phenyl)-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea 
• 63204-11-5 4-isothiocyanato-1,3,5-trimethyl-1H-pyrazole 
• 1215013-68-5 4-bromomethyl-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215011-38-3 4-bromo-3,6-difluoro-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215011-57-6 4-bromo-2-methyl-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215011-59-8 4-bromo-2-fluoro-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 877982-71-3 4-bromo-2-chloro-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215009-29-2 4-bromo-2,6-dichloro-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzenesulfonamide 
• 1215008-91-5 4-(2-methylthiazol-4-yl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215011-19-0 6-(3-(4-benzylpiperazin-1-yl)pyrrolidin-1-yl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)pyridine-3-sulfonamide 

Relevant academic research and scientific papers

BICYCLIC KINASE INHIBITORS AND USES THEREOF

The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family, CSF1R, HCK, TEK-family, BRK, ABL, KIT and/or their mutants. Although structurally similar to other bicyclic kinase inhibitors, the kinase inhibitors of the invention are distinctive; possessing a particular class of heterocyclic moiety. Such kinase inhibitors can display one or more certain properties distinct to their structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally related kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions of the invention may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.

CHEMICAL SUBSTANCES WHICH INHIBIT THE ENZYMATIC ACTIVITY OF HUMAN KALLIKREIN-RELATED PEPTIDASE 6 (KLK6)

The invention relates to compounds which are suitable for the treatment of a disease associated with kallikrein-like peptidase 6 overexpression and to pharmaceutical compositions containing such compounds. The invention further relates to a kit of parts comprising such compounds or pharmaceutical compositions.

Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity

Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6.

SUBSTITUTED PYRIMIDINE COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF

The present disclosure relates to pyrimidine compounds of formula (I), their stereoisomers, tautomers, pharmaceutically acceptable salts, polymorphs, solvates, and hydrates thereof. The present disclosure also relates to process of preparation of these pyrimidine compounds, and to pharmaceutical compositions containing them. The compounds of the present disclosure are useful in the treatment, prevention or suppression of diseases and disorders mediated by epidermal growth factor receptor (EGFR) family kinases.

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts

A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.

Synthesis and biological evaluation of new N-substituted-N′-(3,5-di/ 1,3,5-trimethylpyrazole-4-yl)thiourea/urea derivatives

Several thiourea and urea derivatives were prepared by the reaction of 4-aminopyrazoles with substituted isothiocyanates or isocyanates. The novel compounds were tested anticonvulsant activity using by pentylenetetrazole- induced seizure (PTZ) and maximal electroshock seizure (MES) tests. Among the tested compounds, thiourea derivatives of 4b were afforded 90 and 100% protection in PTZ and MES tests at 50 mg/kg, respectively. Urea derivatives of 5a and 5b were afforded 82 and 100% protection both at 25 and 50 mg/kg. Also synthesized compounds were screened for antituberculosis activity against Mycobacterium tuberculosis H37Rv at 6.25 μg/mL concentration but they were not found active at these concentration. In addition, some selected compounds were evaluated for in vitro anti-HIV activity and they were all negative.

Heterocyclic-substituted alkylamide acat inhibitors

Pharmaceutically useful compounds having ACAT inhibitory activity of the formula wherein n is 0, 1, or 2, for X other than tetrazole and n = 2 then R2 = R3 = H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; x is a 5-membered heteromonocyclic group containing at least one to four heteroatoms selected from the group consisting of isothiazole, oxazole, thiazole, imidazole, furan, thiophene, pyrrole, tetrazole, 1,2,3-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-oxadiazole said heteromonocyclic group being unsubstituted or substituted at any available position along the ring,

Reactions of pyrazoles and pyrazolium salts with complex metal hydrides and organometallic reagents. Synthesis of pyrazolines and pyrazolidines

2-Pyrazolin-4-oximes have been synthesized by reaction of 4-nitroso- and 4-nitropyrazoles with complex metal hydrides and organometallic reagents. Furthermore, 4-nitropyrazolium tetrafluoroborates are reactive substrates towards organolithium and Grignard

Isoxazolyl-substituted alkyl amide ACAT inhibitors

Pharmaceutically useful compounds having ACAT inhibitory activity of the formula STR1 wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R2 =R3 =H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.