cas 605-38-9, 2,3-Pyridinedicarboxylic acid dimethyl ester

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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].
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Paragraph 0493-0496

(2020/08/19)

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.
Melnykov, Kostiantyn P.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.,Rusanov, Eduard B.,Grygorenko, Oleksandr O.
p. 255 - 261
(2018/10/15)

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.
Gras
p. 869 - 879
(2020/01/21)

COMPOUNDS
Disclosed are compounds of the formula (I) and pharmaceutically acceptable salts thereof: (I) wherein R1, R2, R3, R4, R5, R6, R8, R9, X, X1, X2, X3, L1 and n are as defined herein. The compounds are inhibitors of adrenomedullin receptor subtype 2 (AM2). Also disclosed are the compounds for use in the treatment of diseases modulated AM2, including proliferative diseases such as cancer; pharmaceutical compositions comprising the compounds; methods for preparing the compounds;and intermediates useful in the preparation of the compounds.
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Page/Page column 316

(2018/12/13)

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.
Zscherp, Robert,Baumeister, S?ren,Schepmann, Dirk,Wünsch, Bernhard
p. 397 - 404
(2018/08/17)

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.
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Paragraph 0686; 0686-0688

(2017/12/31)

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
Nizami, Tauqir A.,Hua, Ruimao
p. 6080 - 6084
(2017/09/23)

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%.
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Paragraph 0185; 0186; 0187; 0188

(2016/10/10)

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.
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Paragraph 0310; 0311; 0312

(2014/12/09)

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.
Eichler, Mathias C.,Grayson, David H.
p. 38 - 53
(2015/01/08)

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: C1 C1-C4 alkyl, halogen, halo C1-C4 alkyl, C1-C4 alkoxy, CN; P is a 6-membered heteroaryl or a 8-1 1 membered bicylic 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.
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Page/Page column 48; 49

(2013/07/05)

A robust process for an mGluR5 negative allosteric modulator: Difluoromethylation and sonogashira coupling on large scale
The development of the potent and selective mGluR5 negative allosteric modulator (NAM) 1 is described. Key features in the process, which has been implemented on a multikilogram scale, include a high-temperature difluoromethylation reaction, a Sonogashira coupling, and careful control of residual Pd and Cu in the final API. Due to the relative nonpolar nature of the intermediates, water-miscible solvents were employed in all four steps to allow for direct crystallizations upon reaction completion. In addition, several crystalline morphologies of the API were discovered, and the isolation of the desired form II will be discussed.
Sperry, Jeffrey B.,Farr, Roger M.,Levent, Mahmut,Ghosh, Mousumi,Hoagland, Steven M.,Varsolona, Richard J.,Sutherland, Karen
p. 1854 - 1860
(2013/01/15)

SYNTHESIS OF (4aS,7aS)-OCTAHYDRO-1H-PYRROLO[3,4-b]PYRIDINE
The present invention relates to the stereoselective synthesis of (4aS,7aS)-octahydro-1H-pyrrolo [3, 4-b]pyridine, as well as the conversion thereof, to give Moxifloxacin. Particularly, the present invention relates to a method for the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) comprising : (a) the optical resolution by enzymatic hydrolysis of the intermediate dialkyl-1-alkylcarbonylpiperidine-2,3-dicarboxylate racemate of formula (II) to give, following isolation, the intermediate dialkyl-(2S,3R)-1-alkylcarbonyl-piperidine-2,3-dicarboxylate of formula (III) in which AIk is a straight or branched C1-C5 alkyl group; (b) the conversion of the intermediate (III) to (4aR,7aS)-1-alkylcarbonylhexahydrofuro[3, 4-b]pyridine-5,7-dione of formula (IV) in which AIk has the meanings set forth above; (c) the conversion of the intermediate (IV) to (4aS,7as)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) with an optical purity above 99%.
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Page/Page column 27-28

(2010/09/18)

ANTIMICROBIAL HETEROCYCLIC COMPOUNDS FOR TREATMENT OF BACTERIAL INFECTIONS
The present invention provides heterocyclic compounds of the following formula (I) : or pharmaceutically acceptable salts, prodrugs, solvates, or hydrates thereof useful as antibacterial agents, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.
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Page/Page column 60

(2008/12/08)

Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors
HB-EGF Shedding inhibitors have been expected to become effective medicines for skin diseases caused by the proliferation of keratinocytes. In order to discover novel HB-EGF shedding inhibitors and clarify their structure-activity relationships, 5,6,7,8-tetrahydronaphthylidine-based hydroxamic acid and 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids have been synthesized. Among the synthesized compounds, the ethoxyethoxy derivative 3o and the methoxypropoxy derivative 3p exhibited much more potent HB-EGF shedding inhibitory activity than CGS 27023A. The structural modification of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids enabled us to establish the following structure-activity relationships; the existences of the hydroxamic acid, the sulfonamide, and the phenyl moieties are crucial for a potent HB-EGF shedding inhibitory activity, and the stereochemistry of the alpha carbon of hydroxamic acid is also important. In addition, from the comparison of their HB-EGF shedding inhibitory activities with their MMPs inhibitory activities, we found that the S1′ pocket of the responsible enzyme for HB-EGF shedding is deep unlike that of MMP-1.
Yoshiizumi, Kazuya,Yamamoto, Minoru,Miyasaka, Tomohiro,Ito, Yasuko,Kumihara, Hiroshi,Sawa, Masaaki,Kiyoi, Takao,Yamamoto, Takeshi,Nakajima, Fumio,Hirayama, Ryoichi,Kondo, Hirosato,Ishibushi, Etsuko,Ohmoto, Hiroshi,Inoue, Yoshimasa,Yoshino, Kohichiro
p. 433 - 450
(2007/10/03)

Photodetachment of zwitterions: Probing intramolecular coulomb repulsion and attraction in the gas phase using pyridinium dicarboxylate anions
Zwitterions are critically important in many biological transformations and are used in numerous chemical processes. The consequences of electrostatic effects on reactivity and physical properties, however, are largely unknown. In this work, we report the results of negative ion photoelectron spectra of nine isomeric pyridinium dicarboxylate zwitterions and three nonzwitterionic methoxycarbonylpyridine carboxylate isomers (-O2CPyrCO2CH3). Information about the intramolecular electrostatic interactions was directly obtained from the photoelectron spectra. The adiabatic and vertical detachment energies were measured and understood in terms of intramolecular Coulombic forces. Calculations at the B3LYP and CCSD(T) level were performed and compared to the experimental electron binding energies. Structures, relative stabilities, and the electron detachment sites also were obtained from the calculations.
Wang, Xue-Bin,Dacres, Jelena E.,Yang, Xin,Broadus, Katherine M.,Lis, Lev,Wang, Lai-Sheng,Kass, Steven R.
p. 296 - 304
(2007/10/03)

Aza analog of dithio-β-isoindigo
An improved synthesis of 2,3-pyridinedicarboxyic acid is proposed, providing a higher yield of the target product. The acid was used as starting material for the synthesis of dithio-β-isoindigo. The IR and electronic spectra of the latter were studied.
Neustroeva
p. 1823 - 1826
(2007/10/03)

Quinolone derivatives and processes for preparing the same
The present invention relates to quinoline derivatives substituted in the 7-position by a trans-2,8-diazabicyclo?4.3.0!nonan-8-yl group having a broad antibacterial spectrum and to processes for preparing the same.
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(2008/06/13)

Facile access to novel 1,4-dihydroxynaphthalene-2,3-dicarboximides and heterofused analogs
A variety of novel 1,4-dihydroxynaphthalene-2,3-dicarboximides and heterofused analogs were prepared by a convenient one-pot base-catalyzed condensation of N-substituted succinimides with aromatic ortho diester derivatives.
Murray, William M.,Semple, J. Edward
p. 1180 - 1182
(2007/10/03)

HETEROCYCLIC-NMDA ANTAGONISTS
The present invention is directed to a class of 3-phosphono-piperidine and pyrrolidine derivatives and their use as NMDA antagonists.
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(2008/06/13)

Aromatic Ring Cleavage in 6-Methoxyquinolines and 2-Methoxynaphthalene with Fuming Nitric Acid
Two 6-methoxyquinolines and 2-methoxynaphthalene, on prolonged treatment with fuming nitric acid, give major products resulting from benzene ring cleavage but retaining all carbons of the cleaved ring.Methoxyisoquinolines were not cleaved under the same conditions.
Balczewski, Piotr,Morris, Gareth A.,Joule, John A.
p. 2514 - 2523
(2007/10/02)

Heterocyclic Analogues of Phthalhydrazides: Cyclic Hydrazides of Pyridine 1-Oxide and Pyrazine 1,4-Dioxide Dicarboxylic Acids
The synthesis of N-oxides of the cyclic hydrazides of pyridine and pyrazine o-dicarboxylic acids is described.Pyridopyridazine-5,8-dione 1-oxide, pyridopyridazine-1,4-dione 6-oxide, and pyrazinopyridazine-5,8-dione 1,2-dioxide, were obtained by direct oxidation of the parent hydrazides with peracetic acid.The pyridopyridazine derivatives were also unambiguously synthesized by treating the anhydrides or diesters of the relevant carboxylic acid 1-oxides with hydrazine hydrate.
Paul, D. Brenton
p. 87 - 94
(2007/10/02)

PREPARATION AND STRUCTURAL ASSIGNMENTS OF SOME ISOMERIC 2,3-DISUBSTITUTED PYRIDINES
The preparation of several isomeric 2,3-disubstituted pyridine compounds are described and their spectroscopical data given.IR and NMR spectra of quinolinimide, reported by Distefano et al., are contradicted.The electron impact mass spectra are found to be useful in the differentiation between positional isomers.
Spiessens, Luc I. M.,Anteunis, Marc J. O.
p. 205 - 232
(2007/10/02)