- Microwave-assisted synthesis of 2-aminonicotinic acids by reacting 2-chloronicotinic acid with amines
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2-(Methylamino)nicotinic acid was readily prepared in high yield by reacting 2-chloronicotinic acid with 40% aq MeNH2 under microwave irradiation either at 120 °C for 2 h or at 140 °C for 1.5 h. Subsequently, we found that a range of 2-aminonicotinic acids could be obtained under microwave heating. The optimal reaction conditions involved the use of 3 equiv of amine, water as the solvent and heating at 200 °C for 2 h in the presence of diisopropylethylamine (3 equiv).
- Quevedo, Camilo E.,Bavetsias, Vassilios,McDonald, Edward
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experimental part
p. 2481 - 2483
(2009/08/17)
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- SUBSTITUTED NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND THEIR USE IN THE TREATMENT OF HUMAN DISEASES
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Inhibitors of MIF having a naphthyridine backbone are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures: (Ia), (Ib), (Ic), (Id) including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R, R1, R2, X, Y and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.
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Page/Page column 111; 159-160
(2010/02/11)
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- Synthesis of SMP-797: A new potent ACAT inhibitor
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A potent ACAT (acyl-CoA: cholesterol acyltransferase) inhibitor SMP-797 was effectively synthesized by the urea formation of 3-amino-4-aryl-1,8- naphthyridin-2(1H)-one and 4-amino-2,6-diisopropylamine. The synthesis of the former compound involved the Suzuki coupling reaction as a key step, and the latter was prepared by the 4-selective nitration of 2,6-diisopropylaniline using 2,3,5,6-tetrabromo-4-methyl-4-nitro-2,5-cyclohexadienone.
- Ban, Hitoshi,Muraoka, Masami,Ohashi, Naohito
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p. 10081 - 10092
(2007/10/03)
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- OXYTOCIN INHIBITORS
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This invention relates to compounds of formula (I).
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- A convenient synthesis of 4-aryl-1,8-naphthyridin-2(1H)-ones by the Suzuki coupling
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4-Halo-1,8-naphthyridin-2(1H)-ones readily available from 2-chloronicotinic acid were subjected to the Suzuki coupling reaction with arylboronic acids to give a diversity of 4-aryl-1,8-naphthyridin-2(1H)-ones.
- Ban, Hitoshi,Muraoka, Masami,Ohashi, Naohito
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p. 6021 - 6023
(2007/10/03)
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- Naphthyridinone derivatives
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Compounds of formula I STR1 including pharmaceutically acceptable salts thereof in which R1 represents a phenyl C1-6 alkyl group (in which the phenyl ring is optionally substituted by one or more of the following: halo, a C1-4 alkyl group, a C1-4 alkoxy group, hydroxy or trifluoromethyl) and the alkyl chain is optionally substituted by one or more C1-2 alkyl groups; R2 represents a C2-6 alkoxycarbonyl group; and R3 represents hydrogen or halo are disclosed, which are antirheumatic agents and are useful as modulators of cytokine synthesis, immunomodulatory agents, antiinflammatory agents and anti-allergic agents. Compositions containing these compounds and processes to make these compounds are also disclosed.
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- Substituted 1,3-Dihydro-2H-pyrrolopyridin-2-ones as Potential Antiinflammatory Agents
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A series of analogues based on the 1,3-dihydro-2H-pyrrolopyridin-2-one ring system have been synthesized and shown to possess oral antiinflammatory activity in both the reverse passive Arthus reaction (RPAR) pleural cavity assay in rats and in the adjuvant-induced arthritic rat model (AAR).Several members of this series additionally exhibit an inhibitory effect on the in vivo production of prostaglandin- and leukotriene-derived products or arachidonic acid metabolism although these compounds exhibit no significant inhibitory activity against the cyclooxygenase and 5-lipoxygenase enzymes in vitro.Structure-activity relationships in this series are discussed.
- Ting, Pauline C.,Kaminski, James J.,Sherlock, Margaret H.,Tom, Wing C.,Lee, Joe F.,et al.
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p. 2697 - 2706
(2007/10/02)
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- Antiallergy Agents. 1. Substituted 1,8-Naphthyridin-2(1H)-ones as Inhibitors of SRS-A Release
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A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described.The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models.Structure-activity studies of the lead compound in this sereis, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (89).The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.
- Sherlock, Margaret H.,Kaminski, James J.,Tom, Wing C.,Lee, Joe F.,Wong, Shing-Chun,et al.
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p. 2108 - 2121
(2007/10/02)
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