4021-12-9

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-4-PYRIDINECARBOXYLIC ACID is used as a key intermediate in the synthesis of 4,5-dihydro-1H-pyrazole derivatives, which serve as cholesterol 24 hydroxylase inhibitors. These inhibitors are crucial for the prevention and/or treatment of neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease, and other conditions related to cognitive decline.
Used in Neurodegenerative Disease Treatment:
3-METHYL-4-PYRIDINECARBOXYLIC ACID is used as a precursor for the development of novel therapeutic agents targeting cholesterol 24 hydroxylase, an enzyme involved in the metabolism of cholesterol in the brain. Inhibition of this enzyme has been shown to have potential benefits in the treatment of neurodegenerative diseases by modulating cholesterol levels and reducing the formation of toxic metabolites that contribute to neuronal damage.

InChI:InChI=1/C7H7NO2/c1-5-4-8-3-2-6(5)7(9)10/h2-4H,1H3,(H,9,10)

Upstream product

• 7584-05-6 3-methyl-4-cyanopyridine 
• 583-58-4 3,4-Lutidin 
• 116985-92-3 Methyl 3-methylpyridine-4-carboxylate 
• 1681-36-3 4-chloro-3-methylpyridine 
• 88329-56-0 3,N-dimethylisonicotinanilide 

Downstream Products

• 883556-91-0 (4-isopropyl-phenyl)-[5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883556-90-9 (4-tert-butyl-phenyl)-[5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883557-00-4 [4-(chloro-difluoro-methoxy)-phenyl]-[5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883557-02-6 [5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-(4-trifluoromethyl-phenyl)-amine 
• 883556-82-9 [5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-(3-trifluoromethyl-phenyl)-amine 
• 883557-01-5 [5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-(4-trifluoromethoxy-phenyl)-amine 
• 883557-10-6 [5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-(3-trifluoromethoxy-phenyl)-amine 
• 883557-55-9 (4-Isopropyl-phenyl)-{5-[3-((E)-2-pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 883557-54-8 (4-tert-butyl-phenyl)-{5-[3-(2-pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 883557-68-4 {5-[3-((E)-2-Pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethoxy-phenyl)-amine 
• 883557-61-7 [4-(Chloro-difluoro-methoxy)-phenyl]-{5-[3-((E)-2-pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 883557-62-8 {5-[3-((E)-2-Pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-(4-trifluoromethoxy-phenyl)-amine 
• 883557-63-9 {5-[3-((E)-2-Pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-(4-trifluoromethyl-phenyl)-amine 
• 883557-80-0 {5-[3-((E)-2-Pyridin-4-yl-vinyl)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine 

Relevant academic research and scientific papers

COMPOUNDS USEFUL FOR ALTERING THE LEVELS OF BILE ACIDS FOR THE TREATMENT OF DIABETES AND CARDIOMETABOLIC DISEASE

Described herein are compounds of Formula (I) or a pharmaceutically acceptable salt thereof. The compounds of Formula I act as Cyp8b1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for diabetes and cardiovascular disease.

One-Step Synthetic Access to Isosteric and Potent Anticancer Nitrogen Heterocycles with the Benzo[c]phenanthridine Scaffold

A versatile one-step two-component cyclization to build new tetracyclic nitrogen heterocycles is described. Ortho-methylhetarenecarbonitrile components were condensed with aldehydes to access a large library of differently substituted ring systems. The heterocyclic core can be easily modified by variation of the position of the endocyclic nitrogen atom in the o-methylhetarenecarbonitrile substrate. The manner of the nucleophilic attack that leads to the condensation can be triggered by different electron-density distribution in the molecule induced by the position of the nitrogen atom. Taking this into account, there is an electronic preference that leads to either pyridophenanthrolines or the corresponding pyridoazacarbazoles as the main products. We demonstrate the high antitumor potential of some of our synthesized heterocycles, which is strongly dependent on the substitution pattern introduced through the aldehyde component. The position and number of endocyclic nitrogen atoms play an important role regarding cytotoxicity of the studied compounds. Isosteric nitrogen heterocycles: A large library of heterocycles, some possessing promising anticancer properties, with different substitution patterns is accessible by a facile one-step cyclization method through application of different aldehydes and distinct o-methylhetarenecarbonitrile components with diverse numbers of nitrogen atoms at various positions in the ring (see scheme).

AZAINDENOISOQUINOLINE TOPOISOMERASE I INHIBITORS

The invention described herein pertains to substituted azaindenoisoquinoline compounds, in particular 7-, 8-, 9-, and 10-azaindenoisoquinoline compounds, which are inhibitors of topoisomerase I, processes and intermediates for their syntheses, pharmaceutical compositions of the compounds, and methods of using them in the treatment of cancer.

Tetrahydropyrido[d]pyridazinones - Promising scaffolds for drug discovery

An approach to the synthesis of all possible tetrahydropyrido[d] pyridazinones has been developed. The method relies on the catalytic hydrogenation of the corresponding aromatic counterparts, which were obtained by cyclization of the relevant dibromomethyl-substituted pyridinecarboxylates with hydrazine. The synthetic schemes include 4-5 steps starting from commercially available materials. The tetrahydropyrido[d]pyridazinone scaffolds are combinations of a saturated heterocycle (piperidine) and a privileged aromatic heterocycle (pyridazinone); hence they are promising starting points for the design in medicinal chemistry.

Azaindenoisoquinolines as topoisomerase i inhibitors and potential anticancer agents: A systematic study of structure-activity relationships

A comprehensive study of a series of azaindenoisoquinoline topoisomerase I (Top1) inhibitors is reported. The synthetic pathways have been developed to prepare 7-, 8-, 9-, and 10-azaindenoisoquinolines. The present study shows that 7-azaindenoisoquinolines possess the greatest Top1 inhibitory activity and cytotoxicity. Additionally, the introduction of a methoxy group into the D-ring of 7-azaindenoisoquinolines improved their biological activities, leading to new lead molecules for further development. A series of QM calculations were performed on the model "sandwich" complexes of azaindenoisoquinolines with flanking DNA base pairs from the Drug-Top1-DNA ternary complex. The results of these calculations demonstrate how changes in two forces contributing to the π-π stacking (dispersion and charge-transfer interactions) affect the binding of the drug to the Top1-DNA cleavage complex and thus modulate the drug's Top1 inhibitory activity.

Design, synthesis, and biological evaluation of 17-cyclopropylmethyl-3, 14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido] morphinan derivatives as peripheral selective μ opioid receptor agents

Peripheral selective μ opioid receptor (MOR) antagonists could alleviate the symptoms of opioid-induced constipation (OIC) without compromising the analgesic effect of opioids. However, a variety of adverse effects were associated with them, partially due to their relatively low MOR selectivity. NAP, a 6β-N-4′-pyridyl substituted naltrexamine derivative, was identified previously as a potent and highly selective MOR antagonist mainly acting within the peripheral nervous system. The noticeable diarrhea associated with it prompted the design and synthesis of its analogues in order to study its structure-activity relationship. Among them, compound 8 showed improved pharmacological profiles compared to the original lead, acting mainly at peripheral while increasing the intestinal motility in morphine-pelleted mice (ED50 = 0.03 mg/kg). The slight decrease of the ED50 compared to the original lead was well compensated by the unobserved adverse effect. Hence, this compound seems to be a more promising lead to develop novel therapeutic agents toward OIC.

2-PYRIDINYL[7-(SUBSTITUTED-PYRIDIN-4-YL) PYRAZOLO[1,5-A]PYRIMIDIN-3-YL]METHANONES

The present invention provides novel 2-pyridinyl[7(pyridin-4-yl)pyrazolo[1,5--a]pyrimidin-3-yl]methanones with at least one substituent on the 4-pyridinyl ring having the chemical structure of formula (I): The invention further provides compositions and methods employing the novel 2-pyridinyl[7-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]methanones of formula: (I) in to modulate GABA and GABA receptor physiology to elicit therapeutic responses in mammalian subjects to alleviate neurological or psychiatric disorders, including stroke, head trauma, epilepsy, pain, migraine, mood disorders, anxiety, post traumatic stress disorder, obsessive compulsive disorders, mania, bipolar disorders, schizophrenia, seizures, convulsions, tinnitus, neurodegenerative disorders including Alzheimer's disease, amyotrophic lateral sclerosis and Parkinson's disease, Huntington's chorea, depression, bipolar disorders, mania, trigeminal and other neuralgia, neuropathic pain, hypertension, cerebral ischemia, cardiac arrhythmia, myotonia, substance abuse, myoclonus, essential tremor, dyskinesia and other movement disorders, neonatal cerebral hemorrhage, and spasticity, as well as other psychiatric and neurological disorders mediated by GABA and/or GABA receptors.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND BENAMIDE COMPOUNDS AND DRUGS CONTAINING THE SAME

Disclosed are compounds represented by formula (I) which have triglyceride biosynthesis inhibitory activity in the liver and inhibitory activity against the secretion of apolipoprotein B-containing lipoprotein from the liver and particularly have excellent inhibitory activity against the secretion of apolipoprotein B-containing lipoprotein, are free from side effect of accumulation of lipids in the liver, and are useful for the treatment and prevention of hyperlipidemia and arteriosclerotic diseases. In formula (I), R1 and R2 represent alkyl, alkoxy, cycloalkyl, phenyl, alkenyl, alkynyl, or a five- or six-membered saturated or unsaturated heterocyclic ring, or R1 and R2, together with a nitrogen atom to which R1 and R2 are attached, may form a ring; R3 and R4 represent a hydrogen atom, alkyl, a halogen atom, hydroxyl, nitrile, alkoxycarbonyl, alkoxy, or carboxyl; or R2 and R3 may be attached to each other to form -(CH2)m-, -N=CH-, -CH=N-, or -(C1-6 alkyl)C=N-; A, D, E, and G each represent a carbon atom, or any one of A, D, E, and G represents a nitrogen atom with the other three each representing a carbon atom; Q represents a nitrogen atom or a carbon atom; Y represents a group represented by formula (II) wherein X represents a hydrogen atom, group -C(=O)N(R5)R6 or group -C(=O)OR7, R8 is absent or represents a bond, an oxygen atom, a sulfur atom, -SO2-, -SO-, -CH2-CH2-, or - CH=CH-, and R9 and R10 represent a hydrogen atom, alkyl, alkoxy, a halogen atom, or hydroxyl; and Z represents - (CH2)n-, -O-(CH2)i-, or -C(=O)NH-(CH2)i-.

HIV protease inhibitors

HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.