- A Journey through Hemetsberger–Knittel, Leimgruber–Batcho and Bartoli Reactions: Access to Several Hydroxy 5- and 6-Azaindoles
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The preparation of various 5- and 6-azaindoles, heterocyclic structures that are frequently part of molecules in clinical development, and their monohydroxy analogues were described. Different strategies, relying on the de novo pyrrole ring formation, were investigated and, thanks to Hemetsberger–Knittel, Bartoli and Leimgruber–Batcho approaches, 4- and 7-monohydroxy 5- and 6-azaindoles were obtained. The crucial introduction of the oxygen atom was carried out from halogen derivatives, using nucleophilic substitution reactions under basic conditions with or without a copper catalyst. Some preliminary oxidation reactions have shown that it was yet not possible to synthesize the azaquinone indole structure from monohydroxy azaindole, using molecular oxygen in the presence of salcomine as a catalyst.
- Radix, Sylvie,Hallé, Fran?ois,Mahiout, Zahia,Teissonnière, Amélie,Bouchez, Grégoire,Auberger, Ludovic,Barret, Roland,Lomberget, Thierry
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- ANTHRANILAMIDE COMPOUNDS, PROCESS FOR PRODUCING THESE, AND PEST CONTROL AGENT COMPRISING ANY OF THESE
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A novel pest control agent. Also provided are: an anthranilamide compound represented by the formula (I): (I) (wherein A is Y-substituted alkyl or D-substituted carbonyl; Q is optionally R5-substituted 3-pyridyl or optionally R5-substituted 4-pyridyl; R1 is halogeno, optionally X-substituted alkyl, etc.; R2 and R5 each is halogeno, optionally X-substituted alkyl, etc.; R3 and R4 each is hydrogen or alkyl; X is halogeno, optionally halogenated alkoxy, etc.; Y is C3-4 cycloalkyl, etc.; D is alkenyl, etc.; m is an integer of 0-4; and n is 1 or 2); an N-oxide of the compound; and a salt of the compound.
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Page/Page column 33
(2010/11/26)
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- Substituted ring-fused imidazole derivative: GABAA receptors ligands
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Substituted ring-fused imidazole derivatives that bind to GABAA receptors are provided. Such compounds may be used to modulate ligand binding to GABAA receptors in vivo or in vitro, and are particularly useful in the treatment of a v
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- Benzimidazole and pyridylimidazole derivatives
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This invention relates to benzimidazoles, pyridylimidazoles and related bicyclic heteroaryl compounds, all of which may be described by of Formula I The invention is particularly related to such compounds that bind with high selectivity and high affinity to the benzodiazepine site of GABAA receptors. This invention also relates to pharmaceutical compositions comprising such compounds and to the use of such compounds in treatment of certain central nervous system (CNS) diseases. Novel processes for preparing compounds of Formula I are disclosed. This invention also relates to the use of benzimidazoles, pyridylimidazoles and related bicyclic heteroaryl compounds of Formula I in combination with one or more other CNS agents to potentiate the effects of the other CNS agents. Additionally this invention relates to the use such compounds as probes for the localization of GABAA receptors in tissue sections.
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- Cell adhesion-inhibiting antiinflammatory compounds
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Compounds having Formula I are useful for treating inflammation. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of inhibiting/treating inflammatory diseases in a mammal.
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- Chemistry of the Phenoxathiins and Isosterically Related Heterocycles. XXXII. The Synthesis of 2-Azathianthrene and Selected Analogs
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The synthesis of 2-azathianthrene (benzodithiinopyridine), the only remaining monoazathianthrene yet to be reported, is described.Attempts at the direct condensation of disubstituted pyridines with the dianion of 1,2-dimercaptobenzene were generally unsuccessful requiring that the alternative condensation of the dianion with disubstituted pyridine 1-oxides be employed.The title compound was characterized by physical means including 13 C-nmr spectroscopy.One analog, 4-nitro-2-azathianthrene was also studied by X-ray crystallographic means; the molecule crystallized with two molecules in the asymetric unit P21/n, a=20.712(3), b=7.8109(13), c=13.720(2) Angstroem, β=107.880(11) deg, Z=8, the data refined to a final R=0.051 for 3061 reflections.Dihedral angles between the planes of the phenyl rings were 135.00(13) and 132.52(13) deg for the two independent molecules contained in the crystal.Close non-bonded S...O intramolecular contacts were observed in both molecules between the sulfur and nitro-group oxygens.Both nitro groups are twisted out the plane of the pyridine ring and are oriented at angles of 28.75 and 38.82 deg respectively.
- Lam, Wing W.,Martin, Gary E.,Lynch, Vincent M.,Simonsen, Stanley H.,Lindsay, Charles M.,Smith, Keith
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p. 785 - 791
(2007/10/02)
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