On August 14, 2003, Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes published a patent.Application In Synthesis of 4-Bromo-5-ethyl-2-methylpyridine The title of the patent was Preparation of dihydrobenzodiazepin-2-ones as metabotropic glutamate receptor antagonists for the treatment of neurological disorders. And the patent contained the following:
This invention relates to dihydrobenzo[b][1,4]diazepin-2-ones (shown as I; variables defined below; e.g. 7,8-dichloro-4-[3-(pyridin-3-yl)phenyl]-1,3-dihydrobenzo[b][1,4]diazepin-2-one). The invention further relates to medicaments containing these compounds, a process for their preparation as well as their use for preparation of medicaments for the treatment or prevention of acute and/or chronic neurol. disorders, e.g. Alzheimer’s disease. Three examples of pharmaceutical compositions containing I are included. Ki values for 50 examples of I as metabotropic glutamate receptor antagonists are tabulated, e.g. 0.00135 μM for 7,8-dichloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydrobenzo[b][1,4]diazepin-2-one. More than 400 example preparations of I and many example preparations of intermediates are included. For example, 7,8-dichloro-4-[3-(pyridin-3-yl)phenyl]-1,3-dihydrobenzo[b][1,4]diazepin-2-one (310 mg) was prepared from 4,5-dichlorophenylenediamine (0.97 mmol) and 3-oxo-3-[3-(pyridin-3-yl)phenyl]propionic acid tert-Bu ester (0.97 mmol) by refluxing in xylene. For I: X is a single bond or an ethynediyl group; and wherein in case X is a single bond, R1 is H, cyano, halogen, lower alkyl, lower alkoxy, fluoro-lower alkyl, fluoro-lower alkoxy, pyrrol-1-yl, or Ph, which is (un)substituted by one or two substituents halogen, lower alkyl or fluoro-lower alkyl; or in case X is an ethynediyl group, R1 is Ph, which is (un)substituted by one or two substituents halogen, lower alkyl or fluoro-lower alkyl. R2 is H, lower alkyl, lower alkenyl lower alkoxy, halogen, -NR’R”, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, fluoro-lower alkyl, fluoro-lower alkoxy, or lower alkoxy(ethoxy)m; m = 1-4; R’ is H, lower alkyl or C3-C6-cycloalkyl; R” is H, lower alkyl or C3-C6-cycloalkyl; Y is -CH= or =N-; R3 is a six-membered aromatic heterocycle containing 1 to 3-N atoms or a pyridine N-oxide, which rings are (un)substituted by one or two substituents halogen, fluoro-lower alkyl, fluoro-lower alkoxy, cyano, amino, lower alkylamino, lower alkoxy-lower alkylamino, lower hydroxy-lower alkylamino, -(CH2)n-C(O)-OR”, -(CH2)n-C(O)-NR’R”, -(CH2)n-SO2-NR’R”, -(CH2)n-C(NH2):NR”, hydroxy, lower alkoxy, lower alkylthio, C3-C6-cycloalkyl and lower alkyl, which is (un)substituted by fluoro, -NR’R”, hydroxy, lower alkoxy, pyrrolidin-1-yl, azetidin-1-yl, cyano or carbamoyloxy; n = 0-4. The experimental process involved the reaction of 4-Bromo-5-ethyl-2-methylpyridine(cas: 98488-99-4).Application In Synthesis of 4-Bromo-5-ethyl-2-methylpyridine
The Article related to alzheimer disease, anti-alzheimer agents, antipsychotics, biological memory retention defect, cognition enhancers, cognitive disorders, drug delivery systems, homo sapiens, human, metabotropic glutamate receptors role: bsu (biological study, unclassified), biol (biological study) (antagonists), nervous system agents, nervous system disease, psychosis, schizophrenia and other aspects.Application In Synthesis of 4-Bromo-5-ethyl-2-methylpyridine