15366-34-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 1H-PYRAZOLE-3-CARBOXYLATE is used as a key intermediate for the synthesis of androgen receptor (AR) antagonists. These antagonists play a crucial role in the treatment of various conditions related to androgen excess, such as prostate cancer and hirsutism. The compound's ability to interact with the androgen receptor makes it a valuable component in the development of novel therapeutic agents.
Additionally, METHYL 1H-PYRAZOLE-3-CARBOXYLATE is used as a building block in the preparation of pyrazole nucleosides. These nucleosides are important in the field of medicinal chemistry, as they can be used to develop new antiviral, anticancer, and anti-inflammatory drugs. The unique structure of pyrazole nucleosides allows them to target specific biological pathways, making them promising candidates for the treatment of various diseases.

InChI:InChI=1/C5H6N2O2/c1-9-5(8)4-2-3-6-7-4/h2-3H,1H3,(H,6,7)

Upstream product

• 186581-53-3 diazomethane 
• 598-79-8 2-Chloroacrylic acid 
• 60-29-7 diethyl ether 
• 10443-65-9 2-bromo-2-propenoic acid 
• 67-56-1 methanol 
• 1621-91-6 1H-pyrazole-3-carboxylic acid 
• 49846-91-5 methyl 4,5-dihydro-1H-pyrazole-3-carboxylate 
• 546-67-8 lead(IV) tetraacetate 
• 103582-19-0 3-acetoxy-3-methoxycarbonyl-1-pyrazoline 
• 126554-35-6 methyl 2-diazobut-3-enoate 
• 135641-60-0 3,3-bis(methoxycarbonyl)-3H-pyrazole 
• 87879-93-4 4-diazo-1,1,1,2,2-pentafluoro-3-pentafluoroethyl-3-trifluoromethylbutane 
• 292638-85-8 acrylic acid methyl ester 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 138786-89-7 1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrazole-3-carboxylic acid methyl ester 
• 122818-18-2 methyl 1-vinyl-1H-pyrazole-5-carboxylate 
• 122609-01-2 1-Vinyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 135641-78-0 1-ethoxycarbonyl-3-methoxycarbonyl-1H-pyrazole 
• 119458-46-7 2-ethyl-3-methoxycarbonylpyrazole 
• 89943-27-1 N-1-ethyl-3-methoxycarbonylpyrazole 
• 23585-49-1 (1H-pyrazol-3-yl)methanol 
• 85605-94-3 4-fluoro-1H-pyrazole-3-carboxylic acid methyl ester 
• 150017-55-3 1-Aminopyrazol-5-carbonsaeure-methylester 
• 150017-47-3 1-Aminopyrazol-3-carbonsaeure-methylester 
• 17827-61-1 methyl ester of 1-methylpyrazole-3-carboxylic acid 
• 136944-79-1 4-iodo-1H-pyrazole-3-carboxylic acid methyl ester 
• 851204-27-8 1-({5-bromo-2-[(phenylmethyl)oxy]phenyl}methyl)-5-methyl-1H-pyrazole-3-carboxylic acid 
• 7188-95-6 methyl 1-phenyl-1H-pyrazole-3-carboxylate 

Relevant academic research and scientific papers

COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION

Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using same.

THERAPEUTIC INHIBITORY COMPOUNDS

Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting plasma kallikrein. Furthermore, the subject compounds and compositions are useful for the treatment of diseases wherein the inhibition of plasma kallikrein inhibition has been implicated, such as angioedema and the like.

Optimization and biological evaluation of 2-aminobenzothiazole derivatives as Aurora B kinase inhibitors

A strong relationship between abnormal functions of Aurora kinases and tumorigenesis has been reported for decades. Consequently, Aurora kinases serve as potential targets for anticancer agents. Here, we identified aminobenzothiazole derivatives as novel inhibitors of Aurora B kinase through bioisosteric replacement of the previous inhibitors, aminobenzoxazole derivatives. Most of the urea-linked aminobenzothiazole derivatives showed potent and selective inhibitory activity against Aurora B kinase over Aurora A kinase. Molecular modeling indicated that compound 15g bound well to the active site of Aurora B kinase and formed the essential hydrogen bonds. The potent compounds, 15g and 15k, were selected, and their biological effects were evaluated using HeLa cell lines. It was found that these compounds inhibited the phosphorylation of histone H3 at Ser10 and induced G2/M cell cycle arrest. We suggest that the reported compounds have the potential to be further developed as anticancer therapeutics.

ANDROGEN RECEPTOR MODULATING CARBOXAMIDES

Compounds of formula (I) or (II) wherein Rx, Rz, R9, R10, R14, R14′, R15, R15′, A and B are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds possess utility as tissue-selective androgen receptor modulators (SARM) and are useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

4,7-DIHYDRO-PYRAZOLO[1,5-a]PYRAZIN-6-YLAMINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE)

The present invention relates to novel 4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-yl-amine derivatives as inhibitors of beta-secretase, also known as beta-site amyloid cleaving enzyme, BACE, BACE1, Asp2, or memapsin2. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which beta-secretase is involved, such as Alzheimer's disease (AD), mild cognitive impairment, senility, dementia, dementia with Lewy bodies, Down's syndrome, dementia associated with stroke, dementia associated with Parkinson's disease or dementia associated with beta-amyloid.

ANDROGEN RECEPTOR MODULATING CARBOXAMIDES

Compounds of formula (I) wherein Rx, Rz, R9, R10, R14, R14', R15, R15', A and B are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds possess utility as tissue-selective androgen receptor modulators (SARM) and are particularly useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

4,7-DIHYDRO-PYRAZOLO[1,5-a]PYRAZIN-6-YLAMINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE)

The present invention relates to novel 4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-yl- aminederivativesas inhibitors of beta-secretase, also known as beta-site amyloid cleaving enzyme, BACE, BACE1, Asp2, or memapsin2. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which beta-secretaseis involved, such as Alzheimer's disease (AD), mild cognitive impairment, senility, dementia, dementia with Lewy bodies, Down's syndrome, dementia associatedwith stroke, dementia associated with Parkinson's disease or dementia associated with beta- amyloid.

COMPOUNDS FOR TREATING MUSCULAR DYSTROPHY

Compounds of formula (I): wherein X, L1, R1, L2, R2, R3, and R4 are as defined herein, are useful in the treatment or prophylaxis of Duchenne muscular dystrophy, Becker muscular dystrophy, or cachexia.

CALCIUM RECEPTOR MODULATING AGENTS

The present invention relates generally to novel calcimimetic compounds and pharmaceutical compositions comprising them. The invention also relates to methods of treating of diseases or disorders related to the function of the calcium sensing receptor using the compounds represented in Formula I.