92933-47-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Isopropyl-2H-pyrazole-3-carboxylic acid is used as a reactant for the preparation of pyrazole derivatives, which function as partial agonists for the nicotinic acid receptor. This application is crucial in the development of drugs targeting the receptor, potentially leading to treatments for various conditions, including neurological disorders and metabolic diseases.

InChI:InChI=1/C7H10N2O2/c1-4(2)5-3-6(7(10)11)9-8-5/h3-4H,1-2H3,(H,8,9)(H,10,11)

Upstream product

• 64195-85-3 ethyl 2,4-dioxo-5-methylhexanoate 
• 563-80-4 3-methyl-butan-2-one 
• 20577-64-4 methyl 5-methyl-2,4-dioxohexanoate 
• 78208-72-7 5-(1-methylethyl)-1H-pyrazole-3-carboxylic acid ethyl ester 
• 78208-72-7 ethyl 3-isopropyl-1H-pyrazole-5-carboxylate 

Downstream Products

• 141721-97-3 5-Isopropyl-4-nitro-1H-pyrazol-3-carboxylic Acid 
• 78208-72-7 5-(1-methylethyl)-1H-pyrazole-3-carboxylic acid ethyl ester 
• 521300-01-6 5-isopropyl-4-nitro-1⁽²⁾H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

Photoluminescent report on red light emitting europium(III) complexes with heterocyclic acid

Five luminescent europium (III) carboxylate complexes have been synthesized by using ligand 3-isopropylpyrazole-5-carboxylic acid as primary ligand and 4,4’-dimethyl-2,2’-bipyridyl, 2,2’-bipyridyl, 5,6-dimethyl-1,10-phenanthroline and 1,10-phenanthroline as secondary ligands and characterized through various techniques. These complexes exhibit excellent thermal stability and characteristic europium centered photoemission spectra under the excitation of ultraviolet light. Luminescence decay curves, Judd–Ofelt analysis, internal quantum efficiency and energy transfer mechanism have also been discussed. The color coordinates and color purity are calculated to investigate red emission of the complexes. The study results reveal that these complexes can be potentially used as red light emitting materials in various optoelectronic devices.

COMPOUNDS AS HEPATITIS C INHIBITORS AND USES THEREOF IN MEDICINE

Provided herein are compounds as hepatitis C inhibitors and uses thereof in medicine. Specifically, provided herein is a compound of Formula (I) or a stereoisomer, a tautomer, an enantiomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or hepatitis C diseases. Also provided herein are a pharmaceutically acceptable composition containing such compound and a method of treating HCV infection or hepatitis C diseases comprising administering the compound or pharmaceutical composition thereof disclosed herein.

The discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents

Starting from a non-selective pyrazolo-pyrimidone lead, the sequential use of parallel medicinal chemistry and directed synthesis led to the discovery of potent, highly selective, and orally bioavailable PDE9 inhibitors. The availability of these tools allowed for a thorough evaluation of the therapeutic potential of PDE9 inhibition.

Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a

A series of 5-alkyl pyrazole-3-carboxylic acids were prepared and found to act as potent and selective agonists of the human GPCR, GPR109a, the high affinity nicotinic acid receptor. No activity was observed at the highly homologous low affinity niacin receptor, GPR109b. A further series of 4-fluoro-5-alkyl pyrazole-3-carboxylic acids were shown to display similar potency. One example from the series was shown to have improved properties in vivo compared to niacin.

Agonist lead identification for the high affinity niacin receptor GPR109a

A strategy for lead identification of new agonists of GPR109a, starting from known compounds shown to activate the receptor, is described. Early compound triage led to the formulation of a binding hypothesis and eventually to our focus on a series of pyrazole acid derivatives. Further elaboration of these compounds provided a series of 5,5-fused pyrazoles to be used as lead compounds for further optimization.

PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease

The invention provides compounds of Formula (I) the stereoisomers and prodrugs thereof, and the pharmaceutically acceptable salts of the compounds, stereoisomers, and prodrugs, wherein A, P, J, x, and R10 are as defined herein; pharmaceutical compositions thereof; and methods of using the pharmaceutical compositions for the treatment of diseases, including, diabetes, including type 1 and type 2 diabetes, hyperglycemia, dyslipidemia, impaired glucose tolerance, metabolic syndrome, and/or cardiovascular disease.

Pyrazolo[4,3-D]pyrimidines, process for their preparation and methods of use

The invention relates to 3-, 7-disubstituted pyrazolo[4,3-d]pyrimidines represented by the general formula I and pharmaceutically acceptable salts thereof, whereinR3 is selected from the group consisting of alkyl, cycloalkyl,, cycloalkyl alkyl, cycloheter

Pyrazole derivatives as partial agonists for the nicotinic acid receptor

Nicotinic acid as a hypolipidemic agent appears unique due to its potential to increase HDL cholesterol levels to a greater extent than other drugs. However, it has some side effects, among which severe skin flushing is the most frequent and often limits patients' compliance. In a search for novel agonists for the recently identified and cloned G protein-coupled nicotinic acid receptor, we synthesized a series of substituted pyrazole-3-carboxylic acids that proved to have substantial affinity for this receptor. The affinities were measured by inhibition of [3H] nicotinic acid binding to rat spleen membranes. Potencies and intrinsic activities relative to nicotinic acid were determined by their effects on [35S]GTPγS binding to rat adipocyte and spleen membranes. Interestingly, most compounds were partial agonists. In particular, 2-diazabicyclo-[3,3,O 4,8]octa-3,8-diene-3-carboxylic acid (4c) and 5-propylpyrazole-3-carboxylic acid (4f) proved active with Ki values of approximately 0.15 μM and EC50 values of approximately 6 μM, while their intrinsic activity was only ～50% when compared to nicotinic acid. Even slightly more active was 5-butylpyrazole-3-carboxylic acid (4g) with a Ki value of 0.072 μM, an EC50 value of 4.12 μM, and a relative intrinsic activity of 75%. Of the aralkyl derivatives, 4q (5-(3-chlorobenzyl)pyrazole-3-carboxylic acid) was the most active with a relatively low intrinsic activity of 39%. Partial agonism of the pyrazole derivatives was confirmed by inhibition of G protein activation in response to nicotinic acid by these compounds. The pyrazoles both inhibited the maximum effect elicited by 100 μM nicotinic acid and concentration dependently shifted nicotinic acid concentration-response curves to the right, pointing to a competive mechanism of action.

PDE9 inhibitors for treating cardiovascular disorders

The invention relates to PDE9 inhibitors for treating cardiovascular disorders. Preferred PDE9 inhibitors are compounds of formula I wherein R1 is H or C1-6 alkyl, wherein R1 is attached to either N1 or N2; R2 is C1-6 alkyl optionally substituted by hydroxy or alkoxy; C3-7 cycloalkyl optionally substituted by alkyl, hydroxy or alkoxy; a saturated 5-6-membered heterocycle optionally substituted by alkyl, hydroxy or alkoxy; het1 or Ar1; R3 is C1-6 alkyl optionally substituted by 1 or 2 groups independently selected from: Ar2; C3-7cycloalkyl optionally substituted by C1-6alkyl; OAr2; SAr2; NHC(O)C1-6 alkyl; het2; xanthene; and naphthalene.

Synthesis, antibacterial activity and structure-activity relationship of N-substituted 4-diazo-pyrazole-5-carboxamides. 2

A series of 4-diazopyrazole-5-carboxamides 1 d-n has been synthesized and their antibacterial activity against a number of Gram-negative and Gram-positive strains has been tested. Some of the compounds resulted quite active and the whole set allowed to further study the SAR of the class. Substituents in position 5 affect Gram-negative and Gram-positive activities via bulk and electronic properties respectively; position 3 mostly affects the Gram-negative activity, while the presence of the charged diazo group in position 4 is crucial for both antibacterial activities.