- A Novel Diels-Alder Approach to Heavily Substituted Azasugars
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Diels-Alder cycloaddition of an appropriately substituted 1,4-oxazin-2-one with vinylene carbonate followed by the chemical manipulation of the bridged bicyclic lactone cycloadduct affords a heavily functionalised azasugar ring.
- Afarinkia, Kamyar,Bahar, Akmal,Neuss, Judi
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- Synthesis of spirocyclic pyridoazepines as analogues of galanthamine by nucleophilic aromatic substitution of 3-substituted 2-chloropyridines
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In this report we describe the synthesis of spirocyclic pyridoazepines starting from easily available precursors. The key step of our synthesis is an intramolecular nucleophilic aromatic substitution of the appropriate 3-substituted 2-chloropyridines. The final compounds, designed as simplified analogues of the alkaloid galanthamine, showed significant acetylcholinesterase inhibition activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Vanlaer, Sofie,De Borggraeve, Wim M.,Compernolle, Frans
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- Spirocyclic pyridoazepine analogues of galanthamine: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase
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Spirocyclic pyridoazepines, designed as simplified analogues of the alkaloid galanthamine, were synthesised and evaluated as inhibitors of acetylcholinesterase. The key cyclisation step involved internal displacement of 2-chloro or 2-iodopyridine by either nucleophilic aromatic substitution or a Heck reaction. The target compounds showed significant inhibition of acetylcholinesterase but lower than that of galanthamine. This result could be rationalised by comparative docking simulation studies based on the known crystal structure of the acetylcholinesterase-galanthamine complex; multiple hydrogen bonding of a cocrystallised water molecule to both the receptor and the ligand was found to be of crucial importance for effective binding to the active site of the enzyme. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Vanlaer, Sofie,De Borggraeve, Wim M.,Voet, Arnout,Gielens, Constant,De Maeyer, Marc,Compernolle, Frans
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- 6,5-FUSED HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
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The present invention is directed to 6,5-fused heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.
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(2018/07/29)
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- 6,6-FUSED HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
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The present invention is directed to 6,6-fused heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.
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Page/Page column 37
(2018/07/29)
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- HETEROARYL PIPERIDINE ETHER ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
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The present invention is directed to heteroarylpiperidine ether compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.
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Page/Page column 31
(2018/07/29)
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- AZABICYCLO[4.1.0]HEPTANE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
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The present invention is directed to azabicyclo[4.1.0]heptane compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatmen
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Page/Page column 35; 36
(2019/01/06)
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- 6,7-DIHYDRO-5H-PYRROLO[3,4-B]PYRIDIN-5-ONE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
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The present invention is directed to 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-5-one compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.
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Paragraph 0177
(2017/07/14)
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- POSITIVE ALLOSTERIC MODULATORS OF MGLUR2
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The present invention is directed to 5-substituted 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide and 1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2,-dioxide derivatives which are potentiators of metabotropic glutamate receptors, particularly the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved
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(2011/10/03)
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- Synthesis of 5,5′-dialkyl-6,6′-dichloro-2, 2′-bipyridines
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5,5′-Dialkyl-6,6′-dichloro-2,2′-bipyridines were synthesized starting from 3-substituted 2-chloro-6-iodopyridines using Pd-catalyzed coupling conditions. 6-Alkyl-3,5-dichloro-2H-1,4-oxazin-2-ones were excellent precursors for the synthesis of these functionalized 2-iodo-6-chloropyridines. Copyright Taylor & Francis Group, LLC.
- Chandia,Canales,Azocar,Vanlaer,Pawar,De Borggraeve,Costamagna,Dehaen
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experimental part
p. 927 - 939
(2009/08/08)
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- 2,4'-BIPYRIDINYL COMPOUNDS AS PROTEIN KINASE D INHIBITORS USEFUL FOR THE TREATMENT OF IA HEART FAILURE AND CANCER
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The present invention provides novel organic compounds of Formula I: methods of use, and pharmaceutical compositions thereof.
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Page/Page column 79-80
(2010/01/07)
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- PROCESS FOR PREPARING PYRIDONE DERIVATIVES 226
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A route for preparing a compound of formula (I), where X, R1,R2, R7, R8 and R9 are as defined in the specification, is described. Process steps used in the route and novel intermediates prepared during the route are also described and claimed. Compounds of formula (I) are used in the preparation of pharmaceutical compounds, in particular inhibitors of MEK, useful in the treatment of hyperproliferative disease such as cancer and inflammatory conditions.
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Page/Page column 37
(2009/10/09)
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- Investigation of the Diels-Alder cycloadditions of 2(H)-1,4-oxazin-2-ones
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A variety of 5-chloro-2(H)-1,4-oxazin-2-ones bearing a range of substituents at their 3- and 6-positions undergo Diels-Alder cycloaddition as a 2-azadiene component with electron-rich, electron-deficient, and electron-neutral dienophiles. These reactions
- Afarinkia, Kamyar,Bahar, Akmal,Bearpark, Michael J.,Garcia-Ramos, Yesica,Ruggiero, Andrea,Neuss, Judi,Vyas, Maushami
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p. 9529 - 9537
(2007/10/03)
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- 2(H)-1,4-Oxazin-2-ones as ambident azadienes
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3,5-Dichloro-6-phenyl-2(H)-1,4-oxazin-2-one 3, 5-chloro-3,6-dimethyl-2(H)- 1,4-oxazin-2-one 4, 5-chloro-6-methyl-3-phenyl-2(H)-1,4-oxazin-2-one 5 and 5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one 7, are ambident azadienes reacting efficiently and selectivel
- Afarinkia, Kamyar,Bahar, Akmal,Neuss, Judi,Ruggiero, Andrea
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p. 3995 - 3998
(2007/10/03)
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- Synthesis of new [1,2,3]triazoles and 1H-tetrazoles via reactions of 3,(5)-(Di)chloro-2H-1,4-(benz)oxazin-2-ones with diazocompounds or sodium azide
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Treatment of 3,(5)-(di)chloro-2H-1,4-(benz)oxazin-2-ones with diazo compounds or sodium azide yields bi(tri)cyclic compounds which can be converted into [1,2,3]triazoles or 1,5-disubstituted tetrazoles via reactions with nucleophiles as methanol, water and amines.
- Medaer, Bart,Van Aken, Koen,Hoornaert, Georges
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p. 9767 - 9770
(2007/10/02)
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- A General Synthesis of 3,5-Dihalo-2H-1,4-oxazin-2-ones from Cyanohydrins
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In a novel approach starting from O-trimethylsilyl protected or unprotected cyanohydrins and oxalyl chloride or bromide, a series of unknown 6-substituted 3,5-dihalo-2H-1,4-oxazin-2-ones were prepared.The method was shown to be efficient for various types of cyanohydrins; however cyclization was not obtained with cyanohydrins containing bulky substituents, electron-rich aryl or heteroaryl groups.A mechanism is proposed.
- Meerpoel, Lieven,Hoornaert, Georges
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p. 905 - 908
(2007/10/02)
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- SYNTHESIS OF 3,5-DIHALOGENO-2H-1,4-OXAZIN-2-ONES FROM CYANOHYDRINES
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The title compounds 4 were obtained on treatment of cyanohydrines 3 of aliphatic and aryl aldehydes with oxalyl chloride or bromide in chlorobenzene at 90 deg C.Evidence for their structure is given by their spectroscopic data and by the Diels Alder reaction of 4a and 4g with acetylenic dienophiles to yield substituted pyridines.Cycloaddition was also observed with ethene.
- Meerpoel, L.,Hoornaert, G.
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p. 3183 - 3186
(2007/10/02)
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