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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D311-68
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http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D311-68
filingDate 1971-03-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1974-06-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1357633-A
titleOfInvention Chromanone basic ether derivatives
abstract 1357633 Aminoalkoxy-chromanones BEECHAM GROUP Ltd 2 March 1972 [2 March 1971] 5856/71 Heading C2C Novel compounds of the general Formula (I) in which A is a carbonyl, oxime, semi-carbazone or hydrazone group, R 1 and R 2 are each H, or C 1-4 alkyl; one or two of the groups R 3 , R 4 , R 5 and R 6 are basic ether groups of the formula -O.X.Y (where X is C 1-4 alkylene, and Y is piperidyl, pyridyl, morpholino (each of which can be alkyl substituted) or a group -NR 7 R 8 in which R 7 and R 8 are each H, C 1-4 alkyl, aryl or aralkyl or -NR 7 R 8 denotes a heterocyclic ring having 5 to 8 ring atoms); and the remaining groups R 3 to R 6 are each H, halogen, OH, alkyl, C 1-4 alkoxy or C 1-4 acyloxy; and pharmaceutically acceptable acid addition salts and quaternary ammonium derivatives may be obtained by subjecting a compound of the Formula (II) wherein 1 or 2 of the groups R 3 to R 6 are OH and the remaining groups are H, halogen, alkyl, C 1-4 alkoxy or C 1-4 acyloxy, to (a) reaction with an acid, or its derivative of Formula (III) where R 1 and R 2 are H or C 1-4 alkyl, and B is Cl, Br, OH or O.CO.CH=CR 1 R 2 ; (b) etherification of one or two of the R 3 -R 6 groups which is OH to form basic ether group(s) of formula -O.X.Y, steps (a) and (b) being effected in either order; and (c) optionally converting the resulting 4-chromanone into its oxime, semi-carbazone or hydrazone derivative at any stage during or after (a). Preferably step (a) is carried out before step (b). The etherification (b) is preferably effected by reacting the product of (a) with a compound Z-X-Y in which Z is halide, tosylate or mesylate, or by reacting the product of (a) to convert one or two OH groups to -O.X.Z<SP>1</SP> where Z<SP>1</SP> is halogen, alkylsulphonate or arylsulphonate, and reacting the product with HY or an acid addition salt thereof. Pharmaceutical compositions having activity upon the central nervous system comprise compounds of Formula (I) together with one or more pharmacutically acceptable carriers and/or excipients for parenteral or oral use.
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Total number of triples: 40.