401566-79-8

Usage

Uses

1. Used in Pharmaceutical Industry:
1-(3-Methyl-1-phenyl-5-pyrazolyl)piperazine is used as an intermediate for the synthesis of nonracemic γ-bicyclic heteroarylpiperazineand heteroarylpiperidine-substituted prolinylthiazolidines. These compounds are selective and orally active dipeptidylpeptidase 4 (DPP-4) inhibitors, which play a crucial role in the treatment of type 2 diabetes. By inhibiting DPP-4, these compounds help regulate blood glucose levels, making them valuable in the development of antidiabetic agents.
2. Used in Drug Development:
As a key intermediate in the synthesis of DPP-4 inhibitors, 1-(3-Methyl-1-phenyl-5-pyrazolyl)piperazine contributes to the development of novel therapeutics for diabetes management. Its unique structure allows for the creation of various derivatives with potential enhancements in efficacy, selectivity, and oral bioavailability. This makes it an essential component in the ongoing research and development of innovative treatments for type 2 diabetes.

Upstream product

• 59580-39-1 1-(4-methylpiperazine-1-yl)butane-1,3-dione 
• 1131-17-5 5-chloro-3-methyl-1-phenyl-1H-pyrazole 
• 110-85-0 piperazine 
• 17749-24-5 3-oxo-dithiobutyric acid methyl ester 
• 100-63-0 phenylhydrazine 
• 41327-15-5 5-bromo-3-methyl-1-phenyl-1H-pyrazole 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 19735-89-8 3-methyl-1-phenylpyrazolin-5(4H)-one 
• 591-50-4 iodobenzene 
• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 1404559-15-4 C₂₂H₃₀N₆OS 

Relevant academic research and scientific papers

Synthesis and Microbial Evaluation of Some New 1-(3-Methyl-1-phenyl-1Hpyrazol- 5-yl) Piperazine Sulfonamide/Amides

A series of new 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazines bearing sulfonamide and amide derivatives was synthesized starting from 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one through sequential chlorination, SNAr, deprotection followed by coupling with acid chloride/sulfonyl chloride. The structures of the newly synthesized inhibitors 3-19, were confirmed by using spectral analysis. All the synthesized compounds were evaluated against the selected bacterial (Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739) and fungal stains (Candida albicans ATCC 10231 and Aspergillus niger ATCC 6275). The sulfonamide derivatives 4-12 were found inactive toward the tested bacterial/fungal stains, while the amide derivative 14, 16, 17, 18 and 19 showed moderate activity against S. aureus ATCC 6538 bacterial stain.

The optimization of xanthine derivatives leading to HBK001 hydrochloride as a potent dual ligand targeting DPP-IV and GPR119

A series of xanthine compounds derived from the previous hit 20i with modification on the terminal side chain was discovered through ring formation strategy. Systematic optimization of the compounds with rigid heterocycles in the hydrophobic side chain led to the new lead compound HBK001 (21h) with the improved DPP-IV inhibition and moderate GPR119 agonism activity in vitro. As a continuing work to further study the PK and PD profiles, 21h and its hydrochloride (22) were synthesized on grams scale and evaluated on the ADME/T and oral glucose tolerance test (OGTT) in ICR mice. Compound 22 showed the improved bioavailability and blood glucose-lowering effect in vivo compared to its free base 21h probably attributed to its improved solubility and permeability. The preliminary toxicity studies on compound 22 exhibited that the result of mini-Ames was negative and the preliminary acute toxicity LD50 in mice was above 1.5 g/kg, while it showed moderate inhibition on hERG channel with IC50 4.9 μM maybe due to its high lipophilicity. These findings will be useful for the future drug design for more potent and safer dual ligand targeting DPP-IV and GPR119 for the treatment of diabetes.

Preparation method of 5-piperazinyl-3-methyl-1-phenylpyrazole

The invention discloses a preparation method of a Teneligliptin key intermediate 5-piperazinyl-3-methyl-1-phenylpyrazole, and belongs to the technical field of pharmaceutical manufacturing. Accordingto the preparation method disclosed by the invention, 3-

Method for preparing hydrobromic acid teneligliptin

The invention provides a method for preparing hydrobromic acid teneligliptin. The method includes steps of preparing L-hydroxyproline; mixing the L-hydroxyproline and sodium bicarbonate with each other to obtain mixtures, dissolving the mixtures in water, adding acetone into the water, dropping di-tert-butyl dicarbonate into the water, carrying out room-temperature reaction overnight and then treating reaction products to obtain t-butyloxycarboryl-N-hydroxyproline; preparing t-butyloxycarboryl-N-4-oxo-proline from the t-butyloxycarboryl-N-hydroxyproline; preparing (2S)-4-oxo-2-(3-thiazolidine carbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester from the t-butyloxycarboryl-N-4-oxo-proline; preparing compounds III from compounds IV; preparing compounds II from the compounds III; preparing compounds 1-(3-methyl-1-phenyl-1H-pyrazole-5-base) piperazine from the compounds II; preparing intermediates I; preparing the hydrobromic acid teneligliptin from the intermediates I. The method has the advantages that the method is low in cost, and the cost of the method is only two-thirds of the cost of an existing method in the prior art; the yield of the hydrobromic acid teneligliptin is higher than 95%, and the purity of the hydrobromic acid teneligliptin is higher than 98%.

Process for the preparation of teneligliptin

A process for the preparation of teneligliptin.

Preparation method for 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazine

The invention discloses a preparation method for 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazine. The method uses phenylhydrazine and ethyl acetoacetate as starting materials, and obtains a compound I through cyclization, chloride acetylation, substituti

Teneligliptin key intermediate preparation method

The present invention discloses a preparation method of a teneligliptin key intermediate 1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine (compound I), and belongs to the technical field of medicine preparation. According to the method of the present inven

Key intermediate for geleg sandbank 1 - (3-methyl-1-phenyl-5-pyrazolyl) method for the preparation of piperazine

The invention provides a teneligliptin key intermediate 1-(3-methyl-1-phenyl-5-pyrazolyl) piperazine preparation method which is as follows: reacting N-Boc-N-acetyl acetyl piperazine with phenylhydrazine in an organic solvent with Lawesson reagent, and then removing the protection base in the presence of concentrated hydrochloric acid to obtain an teneligliptin key intermediate. The preparation method has the advantages of being high in yield, low in cost, friendly to the environment and the human body, and more suitable for industrial production.