605-38-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Pyridinedicarboxylic acid dimethyl ester is used as a reagent for the preparation of diarylcyclopentenopyridines, which are important as endothelin receptor antagonists. These antagonists play a crucial role in treating various cardiovascular and pulmonary diseases by blocking the action of endothelin, a potent vasoconstrictor peptide.

InChI:InChI=1/C9H9NO4/c1-13-8(11)6-4-3-5-10-7(6)9(12)14-2/h3-5H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 67-56-1 methanol 
• 144-55-8 sodium hydrogencarbonate 
• 938-33-0 8-methoxyquinoline 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 2450-71-7 Propargylamine 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 6623-91-2 6-methoxy-5-nitroquinoline 

Downstream Products

• 4663-94-9 pyridine-2,3-dicarboxamide 
• 4430-77-7 pyrido[2,3-d]pyridazine-5,8(6H,7H)dione 
• 24195-07-1 pyridine-2,3-dicarboxylic acid 2-methyl ester 
• 38070-79-0 2,3-bis(hydroxymethyl)pyridine 
• 32383-02-1 pyridine-2,3-dicarboxylic acid dimethyl ester N-oxide 
• 23513-23-7 cis-(±)-dimethyl piperidine-2,3-dicarboxylate 
• 24195-02-6 pyridine-2,3-dicarboxylic acid 3-methyl ester 
• 100969-79-7 3-carbomethoxy-2-[(N-benzyl)carbamoyl]pyridine 
• 94870-70-9 pyridine-2,3-dicarboxylic acid bis-benzylamide 
• 32207-46-8 6-(4-methoxy-benzoyl)-[1]pyrindine-5,7-dione 
• 45754-12-9 2,3-bis(chloromethyl)-pyridine 
• 523993-95-5 methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate 
• 32383-03-2 6-chloropyridine-2,3-dicarboxylic acid dimethyl ester 
• 517876-58-3 2-phenylthiopyridine-5,6-dicarboxylic anhydride 

Relevant academic research and scientific papers

IDO/TDO Inhibitor

A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, an aliphatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, an aliphatic ring and a heterocyclic ring; X, R1 and R2 represent a substituent on a ring atom constituting ring A; m represents an integer of 0 to 6; X represents, for example, a halogen atom; and R1 and R2 are the same or different and are selected from, for example, the group consisting of groups of formula (a) or formula (b); and in the following formula (a) and formula (b), Y is selected from the group consisting of O, S, and Se, Z is selected from the group consisting of O, S, and Se, n represents an integer of 1 to 8, r represents an integer of 1 to 8, s represents an integer of 1 to 8, R4 represents, for example, —C(═NH)—HN2, and R6 represents, for example, a substituted or unsubstituted aryl group].

A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold

An approach to rel-(4aS,6R,7aR)-octahydro-1H-cyclopenta[b]pyridine-6-carboxylic acid—a bicyclic conformationally restricted γ-aminobutyric acid (GABA) analogue was developed. The eight-step sequence relied on the reaction of 2,3-bis(chloromethyl)pyridine and a C1-binucleophile and the catalytic reduction of the pyridine ring as the key steps and allowed for the preparation of the title compound in 9.0% overall yield. Assessment of the octahydro-1H-cyclopenta[b]pyridine scaffold geometry showed that this template can be considered truly three-dimensional.

Calcitonin gene-related peptide (CGRP) receptor antagonist treatment of migraine

Migraine is ranked as the sixth cause of years lost due to disability, with around 1.04 billion migraine sufferers globally. Triptans are considered the standard for acute migraine treatment, but an important number of migraineurs do not respond to them and these drugs are contraindicated in patients with cardiovascular disease. Migraine therapy is currently undergoing tremendous development, i.e., 5-HT1F receptor agonists (ditans), anti-calcitonin gene-related peptide (CGRP) monoclonal antibodies, and small-molecule CGRP receptor antagonists (gepants). Ubrogepant (MK-1620) is a small-molecule, potent and selective CGRP receptor antagonist. In two phase III clinical trials (ACHIEVE I and II), ubrogepant showed, at 2 hours, significant percentages of pain freedom, and absence of the most bothersome symptoms in migraine patients. In a phase III study to assess the long-term (52-week) safety and tolerability, ubrogepant displayed good tolerability, and no signs of hepatic toxicity. In March 2019, the U.S. Food and Drug Administration accepted the new drug application (NDA) for ubrogepant for the acute treatment of migraine.

Pyridine bioisosteres of potent GluN2B subunit containing NMDA receptor antagonists with benzo[7]annulene scaffold

It has been reported that benzo [7]annulen-7-amines bearing electron withdrawing substituents such as 3d with a 2-Cl or 3e with a 2-NO2 moiety show very high affinity towards the ifenprodil binding site of GluN2B subunit containing NMDA receptors. Therefore, bioisosteres of 3 with an electron deficient pyridine ring instead of the chloro- or nitrobenzene ring were envisaged. Starting from pyridine-2,3-dicarboxylic acid (5) a five-step synthesis of the key intermediate, the ketone 10, was developed. Reductive amination with various primary amines and NaBH(OAc)3 led to the homologous secondary amines 11a-c. Subsequent methylation yielded the tertiary amines 12b and 12c. Receptor binding studies with [3H]ifenprodil revealed Ki-values above 100 nM for the most active phenylpropyl- and phenylbutylamines 11b and 11c. The >100-fold reduced GluN2B affinity of pyridines 11b and 11c compared to the GluN2B affinity of the corresponding chloro- and nitrobenzene derivatives 3d and 3e indicates that the pyridine ring is not tolerated as bioisosteric replacement of the chloro- or nitrobenzene ring in this type of compounds.

ANTI-PULMONARY TUBERCULOSIS NITROIMIDAZOLE DERIVATIVE

Disclosed is a substituted nitroimidazole derivative, which is mainly used for treating related diseases caused by mycobacterial infections, such as Mycobacterium tuberculosis, especially being suitable for diseases caused by resistant Mycobacterium tuberculosis.

Silver-catalyzed chemoselective annulation of propargyl amines with alkynes for access to pyridines and pyrroles

The annulation of propargyl amines with electron-deficient alkynes in the presence of silver salts affording pyridines and pyrroles has been developed. The chemoselective [4+2] or [3+2] annulation approach to pyridines or pyrroles depends on the structure

Preparation method of (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane

The invention discloses a preparation method of (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane and belongs to the field of the preparation method of a moxifloxacin intermediate. The preparation method comprises eight processes. A resolving process is carried out in initial of the preparation method, in the third process, an ester is resolved to form a chiral intermediate and then through a simple chemical reaction, the (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane is prepared. The invention provides the preparation method utilizing an effective and economic synthesis route to prepare the high-chiral purity (S, S)-2, 8-diazabicyclo[4, 3, 0]nonane. The preparation method is free of an expensive resolving agent and greatly reduces a process cost. In the whole technology, the intermediate is not purified and the crude product can be directly used. The preparation method has simple processes and a high overall yield and can produce the product with chiral purity of 99%.

CHEMICAL COMPOUNDS

The invention relates to a novel compound of formula (I) or a stereoisomer, or a racemate or a mixture or a pharmaceutically acceptable salt thereof: wherein: R is phenyl or a 5- or 6-membered heteroaryl ring containing 1 to 3 heteroatoms selected from S, N and O, such rings may be optionally substituted with n groups Q; Q is selected from a group consisting of: C1-C4 alkyl, halogen, halo C1-C4 alkyl, C1-C4 alkoxy, CN, SO2CH3 or a group —O[(CR1R2]pQ1; or Q may be a group Q2; Q1 is phenyl, which may be optionally substituted with n substituents selected from a group consisting of: C1-C4 alkyl, halogen, halo C1-C4 alkyl, C1-C4 alkoxy, CN, or a group Q2; or corresponds to 2,2-difluoro-benzo[d][1,3]dioxol-4-yl; Q2 is a 5- or 6-membered heteroaryl containing at least one nitrogen atom, which may optionally substituted with n substituents selected from a group consisting of: Cl C1-C4 alkyl, halogen, halo C1-C4 alkyl, C1-C4 alkoxy, CN; P is a 6-membered heteroaryl or a 8-1 1 membered bicyclic heteroaryl group, which may be substituted with n substituents selected from a group consisting of: C1-C4 alkyl, halogen, halo C1-C4 alkyl, C1-C4 alkoxy, CN; R1 is hydrogen or C1-C3 alkyl; R2 is hydrogen or C1-C3 alkyl; n is 1, 2 or 3; p is 0, 1 or 2; and with the proviso that when R corresponds to phenyl, P is substituted by at least one CF3; processes for the preparation of those compounds, pharmaceutical compositions containing one or more compounds of formula (I) and their use as dual antagonists of the Orexin 1 and Orexin 2 receptors.

Ozonolysis of some 8-alkoxyquinolines, and synthesis of a precursor to the non-sedating antihistamine Claritin

3-Formyl-2-methoxycarbonylpyridine and isopropyl 3-formylpyridine-2-carboxylate have each been efficiently accessed in one step via the ozonolyses of 8-methoxy- or of 8-isopropoxyquinoline under near-ambient conditions. The compounds can be utilized as intermediates for syntheses of the tricyclic ketone 8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one, a precursor to the important non-sedating antihistamine Claritin.