cas 1620-77-5, 2-Cyano-5-methylpyridine | Articles data

Articles about 1620-77-5Total 30 be found

Article title
Article abstract
Author
Journal number and time
Download

Compounds with Bridgehead Nitrogen
The position of conformational equilibra in 1,5-,1,6- and 1,8-dimethylperhydro-oxazolopyridines were determined by 1H NMR spectroscopy.The cis-(H-5,H-8a)-1,5-dimethylperhydro-oxazolopyridines adopted the trans fused conformation, as did the two isomers of cis-(H-1,H-8a)-1,6-dimethyl-perhydro-oxazolopyridine.In contrast, r-1,t-6,t-8a-1,6-dimethyl-perhydro-oxazolopyridine preferred the cis-fused conformation.Three of the 1,8-dimehylperhdro-oxazolopyridines adopted the trans-fused conformations (with distortion of the system in the case of the r-1,c-8,c-8a derivative) and the r-1,c-8,c-8a-1,8-dimethyl derivative adopted the cis-fused conformation.
Crabb, Trevor A.,Heywood, Geoffrey C.
p. 242 - 248
(1982)
Read Online

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information
p. 7683 - 7689
(2020/04/22)

Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates
In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance. Copyright
Wang, Ye,Yamaguchi, Kazuya,Mizuno, Noritaka
supporting information; experimental part
p. 7250 - 7253
(2012/08/28)

NOVEL PYRIDINE DERIVATIVES
The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
-
Page/Page column 44

(2013/02/27)

PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS
The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
-
Page/Page column 100

(2013/02/27)

A COMPOUND FOR INHIBITING HUMAN 11-β-HYDROXY STEROID DEHYDROGENASE TYPE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
The present invention relates to a novel compound, or a stereoisomer, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition for human-11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) comprising the same. The invention provides a compound, which has excellent activity and solubility and is more efficiently formulated and delivered, and a pharmaceutical composition for human-11-beta-hydroxysteroid dehydrogenase type 1 comprising the same.
-
Page/Page column 41-42

(2012/10/08)

Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6]
Efficient cyanation of aryl halides is achieved using less toxic K 4[Fe(CN)6] as the reagent and amino-β-cyclodextrins as supramolecular ligands for CuI. Four different amino cyclodextrins viz. per-6-amino-β-CD, per-6-methylamino-β-CD, per-6-butyl-amino-β-CD and mono-6-amino-β-CD are prepared and studied. Aryl and heteroaryl nitriles are obtained in good to excellent yield for even bromo derivatives of flavone and 2-aminopyrans. This system uses catalytic amounts (10 mol%) of both copper iodide and per-6-amino-β-cyclodextrin. Easy separation, the absence of nitrogen atmosphere and excellent yield are the other significant outcomes of this protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Azath, Ismail Abulkalam,Suresh, Palaniswamy,Pitchumani, Kasi
supporting information
p. 2334 - 2339
(2013/01/15)

NOVEL FXR (NR1H4 ) BINDING AND ACTIVITY MODULATING COMPOUNDS
The present invention relates to compounds which bind to the NR1 H4 receptor (FXR) and act as agonists of the NR1 H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.
-
Page/Page column 57; 58

(2011/04/13)

Novel FXR (NR1H4) binding and activity modulating compounds
The present invention relates to compounds which bind to the NR1H4 receptor (FXR) and act as agonists of the NR1H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.
-
Page/Page column 26

(2011/04/14)

Reduction of a redox-active ligand drives switching in a Cu(I) pseudorotaxane by a bimolecular mechanism
The reduction of a redox-active ligand is shown to drive reversible switching of a Cu(I) [2]pseudorotaxane ([2]PR + ) into the reduced [3]pseudorotaxane ([3]PR + ) by a bimolecular mechanism.The unreduced pseudorotaxanes [2]PR + and [3]PR 2+ are initially self-assembled from the binucleating ligand, 3,6-bis(5-methyl-2-pyridine)-1,2,4, 5-tetrazine (Me 2 BPTZ), and a preformed copper-macrocycle moiety (Cu-M + ) based on 1,10-phenanthroline. X-raycrystallography revealed a syn geometry of the [3]PR 2+ .The U V-vis-NIR spectra show low-energy metal-to-ligand charge-transfer transitions that red shift from 808 nm for [2]PR+ to 1088 nm for [3]PR 2+ . Quantitative analysis of the UV-vis-NIR titration shows the stepwise formation constants to be K 1 = 8.9 × 10 8 M -1 and K 2 = 3.1 × 10 + M -1, indicative of negative cooperativity. The cyclic voltammetry (CV)and coulometry of Me 2 BPTZ, [2]PR + , and [3]PR 2+ shows the one-electron reductions at E 1/2 = -0.96, -0.65, and -0.285 V, respectively, to be stabilized in a stepwise manner by each Cu+ ion. CVs of [2]PR + show changes with scan rate consistent with an EC mechanism of supramolecular disproportionation afterreduction: [2]PR 0 + [2]PR + = [3]PR + + Me 2 BPTZ 0 (K D * , Ad). UV-vis- NIR spectroelectrochemistry was used to confirm the 1:1 product stoichiometry for [3]PR + :Me 2 BPTZ. The driving force (δG D = -5.1 kcal mol -1 ) for the reaction is based on the enhanced stability of the reduced [3]PR + over reduced [2]PR 0 by 365 mV (8.4 kcal mol -1 ). Digital simulations of the CVs are consistent with a bimolecular pathway (K d = 12 000 s + M -1 ). Confirmation of the mechanism p rovides a basis to extend this new switching modality to molecular machines.
McNitt, Kristy A.,Parimal, Kumar,Share, Andrew I.,Fahrenbach, Albert C.,Witlicki, Edward H.,et al.
supporting information; experimental part
p. 1305 - 1313
(2009/06/28)

Pd/C-catalyzed cyanation of aryl halides in aqueous PEG
An environmentally friendly Pd/C-PEG-H2O system was developed for the cyanation of aryl halides under microwave irradiation. A wide range of aryl bromides, iodides, and some activated chlorides were demonstrated to be cyanated smoothly by using nontoxic K4[Fe(CN)6] ·3H2O as the cyanide source. There is no phosphorus- or nitrogen-containing ligand or solvent involved. Moreover, this reaction can be carried out without the protection of inert atmosphere. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Chen, Gong,Weng, Jiang,Zheng, Zhanchao,Zhu, Xinhai,Cai, Yaoyao,Cai, Jiwen,Wan, Yiqian
scheme or table
p. 3524 - 3528
(2009/04/07)

HETEROCYCLIC DERIVATIVES
The invention relates to novel heterocyclic derivatives, processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction and heart failure development.
-
Page/Page column 28-29

(2010/02/13)

DIHYDROPYRIDINONE DERIVATIVES
The invention relates to novel dihydropyridinone derivatives, processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction and heart failure development.
-
Page 80-81

(2010/02/06)

NEW COMPOUNDS
The present invention relates to new compounds of formula I, wherein P Q X1 X2 X3 X4 X5 R R1 R2 R3 R4R5 G M1 M2 M3 m and n are defined as in formula I, a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.
-
Page 69

(2010/02/06)

PYRIMIDINONE DERIVATIVES AS THERAPEUTIC AGENTS AGAINST ACUTE AND CHRONIC INFLAMMATORY, ISCHAEMIC AND REMODELLING PROCESSES
The invention relates to novel heterocyclic derivatives, processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases.
-
Page 36

(2010/02/06)

Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.
-
(2008/06/13)

Efficacious and orally bioavailable thrombin inhibitors based on a 2,5-thienylamidine at the P1 position: Discovery of N-carboxymethyl-D-diphenylalanyl-L-prolyl[(5-amidino-2- thienyl)methyllamide
Thrombin, a crucial enzyme in the blood coagulation, has been a target for antithrombotic therapy. Orally active thrombin inhibitors would provide effective and safe prophylaxis for venous and arterial thrombosis. We conducted optimization of a highly efficacious benzamidine-based thrombin inhibitor LB30812 (3, Ki = 3 pM) to improve oral bioavailability. Of a variety of arylamidines investigated at the P1 position, 2,5-thienylamidine effectively replaced the benzamidine without compromising the thrombin inhibitory potency and oral absorption. The sulfamide and sulfonamide derivatization at the N-terminal position in general afforded highly potent thrombin inhibitors but with moderate oral absorption, while the well-absorbable N-carbamate derivatives exhibited limited metabolic stability in S9 fractions. The present work culminated in the discovery of the N-carboxymethyl- and 2,5-thienylamidine-containing compound 22 that exhibits the most favorable profiles of anticoagulant and antithrombotic activities as well as oral bioavilability (Ki = 15 pM; F = 43%, 42%, and 15% in rats, dogs, and monkeys, respectively). This compound on a gravimetric basis was shown to be more effective than a low molecular weight heparin, enoxaparin, in the venous thrombosis models of rat and rabbit. Compound 22 (LB30870) was therefore selected for further preclinical and clinical development.
Lee, Koo,Park, Cheol Won,Jung, Won-Hyuk,Park, Hee Dong,Lee, Sun Hwa,Chung, Kyung Ha,Park, Su Kyung,Kwon, O. Hwan,Kang, Myunggyun,Park, Doo-Hee,Lee, Sang Koo,Kim, Eunice E.,Yoon, Suk Kyoon,Kim, Aeri
p. 3612 - 3622
(2007/10/03)

A process for the preparation of 4-[2-(aryl or heterocyclo)-1H-imidazol-1-yl]benzenesulfonamides
A process to make a compound of the formula or a pharmaceutically acceptable salt thereof is disclosed wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkaxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R4 is a radical selected from hydrido, alkyl and halo; and wherein R2 is selected from aryl and heterocyclo, wherein R2 is optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; ???said method comprising the steps of forming a (protected sulfonyl)benzenamine, treating said (protected sulfonyl)benzenamine first with a base and then with a nitrile to form an amidine, treating said amidine with a haloketone derivative in the presence of a base to form a hydroxyimidazole, forming a (protected sulfonylphenyl) imidazole by dehydrating said hydroxyimidazole, and forming said compounds by deprotecting said (protected sulfonylphenyl)imidazole.
-
Page 67

(2010/01/31)

Orally available peptidic thrombin inhibitors
The present invention relates to novel thrombin inhibitors that are useful as anticoagulants. More particularly, the present invention is directed to peptide derivatives having high antithrombotic activity and high oral bioavailability.
-
(2008/06/13)

Noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1
A series of noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1 was investigated. While the amidrazone and the amine series displayed limited oral absorption, the amidine series demonstrated generally good oral absorption and strong antithrombotic activity; the single-digit picomolar Ki achieved from this series is among the best yet reported. The present work highlights the benzamidine compound 11f (LB30812) that exhibits excellent overall profiles of potency, oral absorption and antithrombotic efficacy.
Lee, Koo,Jung, Won-Hyuk,Park, Cheol Won,Park, Hee Dong,Lee, Sun Hwa,Kwon, O Hwan
p. 1017 - 1022
(2007/10/03)

Selective cyclooxygenase-2 inhibitors: Heteroaryl modified 1,2-diarylimidazoles are potent, orally active antiinflammatory agents
A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2.3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no GI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.
Khanna,Yu,Huff,Weier,Xu,Koszyk,Collins,Cogburn,Isakson,Koboldt,Masferrer,Perkins,Seibert,Veenhuizen,Yuan,Yang,Zhang
p. 3168 - 3185
(2007/10/03)

Cobalt(I)-Catalyzed Cocyclotrimerization of Acetylene with 2,6-Dicyanopyridines
A procedure of general application to the synthesis of alkyl-substituted 2-cyano-6-(2-pyridyl)pyridines from alkylpyridines is outlined.
Chelucci, Giorgio,Cabras, M. Antonietta,Saba, A.
p. 1289 - 1292
(2007/10/02)

Process for the preparation of 2-pyridinecarboxylic acid derivatives and 1-amino-1,4-dihydropyridine-2-carboxylic acid derivatives
The process of the invention relates to the reaction of hydrazones of formula II STR1 with α-chloro- or α-bromoarylonitrile or α-chloro- or α-bromoacrylates of formula III STR2 to 1-amino-2-cyano-1,4-dihydropyridines or 1-amino-1,4-dihydropyridine-2-carboxylic acid esters of formula IV STR3 which are converted into pyridine derivatives of formula I STR4 by treatment with an acid, with removal of R4 R5 NH. Y is --CN or --COOR3 and R1 to R5 may be alkyl.
-
(2008/06/13)

A SHORT SYNTHESIS OF FUSARIC ACID AND ANALOGUES
Fusaric acid (5-n-butyl-pyridine-2-carboxylic acid) and other substituted picolinic acid derivatives aresynthesiyed in two steps from readily avaliable α,β/unsaturated hzdrazones and 2-chloroacrylonitrile in high yield.
Waldner, Adrian
p. 2371 - 2374
(2007/10/02)

Naphtho-[1,2-b]-quinolizium derivatives as antidiarrheal agents
There are disclosed certain naphtho-[1,2-b]-quinolizium compounds which have antidiarrheal activity. The compounds reduce fluid accumulation caused by enterotoxins produced by bacteria such as Vibrio cholerae or Escherichia coli.
-
(2008/06/13)

Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile
The cyanation of 3-halo-, 3-methoxy-, and 3-dimethylaminopyridine 1-oxide with trimethylsilanecarbonitrile gave predominantly the corresponding 3-substituted 2-pyridinecarbonitriles.The deoxygenation of nitropyridine 1-oxides to nitropyridines with the same reagent is also described.Keywords - site-selective reaction; trimethylsilanecarbonitrile; pyridine 1-oxide; 2-pyridine-carbonitrile; nitropyridine 1-oxide; deoxygenation; aromatic amine N-oxide; cyanation
Sakamoto, Takao,Kaneda, Soh-ichi,Nishimura, Sumiko,Yamanaka, Hiroshi
p. 565 - 571
(2007/10/02)

1-ACYLOXYPYRIDINIUM ION: THE REACTIVE INTERMEDIATE IN A MODIFIED REISSERT-HENZE REACTION
Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilanecarbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (ca.90percent) contaminated with 5-methyl-2-pyridinecarbonitrile (ca.10percent) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3.These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.
Fife, Wilmer K.,Boyer, Brett D.
p. 1121 - 1124
(2007/10/02)

Trimethylsilanol as Leaving Group; III. A Simple One-Step Conversion of Aromatic Heterocyclic N-Oxides to α-Cyano Aromatic N-Heterocycles
-
Vorbrueggen, Helmut,Krolikiewicz, Konrad
p. 316 - 319
(2007/10/02)

Regioselective Cyanation of Pyridine 1-Oxides with Trimethylsilanecarbonitrile: A Modified Reissert-Henze Reaction
-
Fife, Wilmer K.
p. 1375 - 1377
(2007/10/02)

Studies on the ammoxidation of N heterocyclic compounds. IV. Vapor phase ammoxidation of lutidine isomers
-
Okada,Morita,Miwa
p. 2402 - 2406
(2007/10/04)