923283-54-9

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate is used as a building block in the synthesis of various pharmaceuticals and organic compounds. Its derivatives have potential applications in the development of new drugs due to its unique chemical structure and properties.
Used in Agrochemical Industry:
Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate is used as a starting material for the development of new agrochemicals. Its antibacterial and antifungal properties make it a promising candidate for use in the creation of effective pesticides and fungicides.
Used in Organic Chemistry Research:
As an important intermediate in organic chemistry, Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate is used in various research applications to explore its reactivity and potential for forming new compounds with diverse applications.

Upstream product

• 138786-86-4 4-nitro-2H-pyrazole-3-carboxylic acid methyl ester 
• 138786-86-4 methyl 4-nitro-1H-pyrazole-3-carboxylate 
• 74-88-4 methyl iodide 
• 309740-49-6 methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate 

Downstream Products

• 939979-32-5 5,7-dichloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine 
• 83824-38-8 1-methyl-1H-pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)-dione 
• 1021497-91-5 4-[2-(4-bromo-phenylsulfanyl)-acetylamino]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Novel pyrazolo[4,3-d]pyrimidine microtubule targeting agents (MTAs): Synthesis, structure–activity relationship, in vitro and in vivo evaluation as antitumor agents

The design, synthesis, and biological evaluation of a series novel N1?methyl pyrazolo[4,3-d]pyrimidines as inhibitors of tubulin polymerization and colchicine binding were described here. Synthesis of target compounds involved alkylation of the pyrazolo scaffold, which afforded two regioisomers. These were separated, characterized and identified with 1H NMR and NOESY spectroscopy. All compounds, except 10, inhibited [3H]colchicine binding to tubulin, and the potent inhibition was similar to that obtained with CA-4. Compounds 9 and 11–13 strongly inhibited the polymerization of tubulin, with IC50 values of 0.45, 0.42, 0.49 and 0.42 μM, respectively. Compounds 14–16 inhibited the polymerization of tubulin with IC50s near ～1 μM. Compounds 9, 12, 13 and 16 inhibited MCF-7 breast cancer cell lines and circumvented βIII-tubulin mediated cancer cell resistance to taxanes and other MTAs, and compounds 9–17 circumvented Pgp-mediated drug resistance. In the standard NCI testing protocol, compound 9 exhibited excellent potency with low to sub nanomolar GI50 values (≤10 nM) against most tumor cell lines, including several multidrug resistant phenotypes. Compound 9 was significantly (P 0.0001) better than paclitaxel at reducing MCF-7 TUBB3 (βIII-tubulin overexpressing) tumors in a mouse xenograft model. Collectively, these studies support the further preclinical development of the pyrazolo[4,3-d]pyrimidine scaffold as a new generation of tubulin inhibitors and 9 as an anticancer agent with advantages over paclitaxel.

5-MORPHOLIN-4-YL-PYRAZOLO[4,3-B]PYRIDINE DERIVATIVES

Compounds of the formula Ia and Ib in which R1, R2 and R3 have the meanings indicated in Claim 1, are inhibitors of ATR, and can be employed for the treatment of diseases such as cancer.

Design, Synthesis, and Physicochemical and Pharmacological Profiling of 7-Hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide Derivatives with Antiosteoarthritic Activity in Vivo

The hallmark of joint diseases, such as osteoarthritis (OA), is pain, originating from both inflammatory and neuropathic components, and compounds able to modulate the signal transduction pathways of the cannabinoid type-2 receptor (CB2R) can represent a helpful option in the treatment of OA. In this perspective, a set of 18 cannabinoid type-2 receptor (CB2R) ligands was developed based on an unprecedented structure. With the aim of improving the physicochemical properties of previously reported 4-hydroxy-2-quinolone-3-carboxamides, a structural optimization program led to the discovery of isosteric 7-hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide derivatives. These new compounds are endowed with high affinity for the CB2R and moderate to good selectivity over the cannabinoid type-1 receptor (CB1R), associated with good physicochemical characteristics. As to the functional activity at the CB2R, compounds able to act either as agonists or as inverse agonists/antagonists were discovered. Among them, compound 51 emerged as a potent CB2R agonist able to reduce pain in rats carrying OA induced by injection of monoiodoacetic acid (MIA).

Pyrazolo[4,3-d]pyrimidines as Antitumor Agents

A compound of Formula I, or optionally a salt or a hydrate of the compound of Formula I is provided: wherein X is one selected from the group consisting of wherein R is an alkyl group having from one to six carbon atoms, and wherein R2 is a halogen atom. A pharmaceutical composition comprising a compound of Formula I, or optionally a salt or a hydrate of the compound of Formula I, and a pharmaceutically acceptable carrier, is provided. A method of treating a patient with cancer is set forth including administering a therapeutically acceptable amount of the compound of Formula I, or a salt or a hydrate of the compound of Formula I, or a pharmaceutical composition comprising a compound of Formula I.

Discovery of novel serine palmitoyltransferase inhibitors as cancer therapeutic agents

We pursued serine palmitoyltransferase (SPT) inhibitors as novel cancer therapeutic agents based on a correlation between SPT inhibition and growth suppression of cancer cells. High-throughput screening and medicinal chemistry efforts led to the identification of structurally diverse SPT inhibitors 4 and 5. Both compounds potently inhibited SPT enzyme and decreased intracellular ceramide content. In addition, they suppressed cell growth of human lung adenocarcinoma HCC4006 and acute promyelocytic leukemia PL-21, and displayed good pharmacokinetic profiles. Reduction of 3-ketodihydrosphingosine, the direct downstream product of SPT, was confirmed under in vivo settings after oral administration of compounds 4 and 5. Their anti-tumor efficacy was observed in a PL-21 xenograft mouse model. These results suggested that SPT inhibitors might have potential to be effective cancer therapeutics.

HYDROXYL PURINE COMPOUNDS AND USE THEREOF

Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers thereof or pharmaceutically acceptable salts thereof.

HETEROCYCLIC COMPOUND

The present invention relates to a compound which can be useful for the treatment or prevention of SPT-related diseases including cancer and congenital diseases associated with sphingolipid accumulation (including Niemann-Pick disease).

Tankyrase inhibitor

The invention belongs to the technical field of medicines and particularly relates to a tankyrase inhibitor represented by a general formula (I) shown in the description and pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof, wherein R1, R2, R3, m, n, Z, L, Q, A, X1, X2 and Y are as defined in the description. The invention further relates to a preparation method for the compounds, pharmaceutical preparations and pharmaceutical compositions containing the compounds and application of the compound and the pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof in preparation of drugs for treating and/or preventing tankyrase mediated cancers and related diseases.

AMINOPYRAZOLE DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF, AND COMPOSITION FOR PREVENTING OR TREATING ISCHEMIC DISEASES CONTAINING THE SAME

Provided are aminopyrazole derivatives, a process for the preparation thereof, and a composition for preventing or treating an ischemic disease containing the same. Since the aminopyrazole derivatives of the present invention can reduce an ischemic cell d

HETEROCYCLIC MODULATORS OF TGR5

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of modulation of TGR5 activity in a human or animal subject are also provided for the treatment diseases mediat