http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1143819-A

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publicationNumber GB-1143819-A
abstract 1,143,819. Hydrogenated benzopyrano [3,4 - of pyridines and process for the preparation thereof. DOW CHEMICAL CO. 16 Sept., 1966 [27 Sept., 1965],No.41570/66. Heading C2C. Novel compounds of general Formula I and of Formula II or an acid-addition or quaternary ammonium salt thereof, wherein R 1 and R 3 are each loweralkyl; R 2 is alkyl or cycloalkyl-lower-alkyl; and R 4 is hydrogen, lower-alkyl, lower-alkanoyl, carbamyl, N-lower-alkyl-carbamyl, N,N-dilower-alkylcarbamyl, or phosphonyl, are prepared by reacting a compound having the Formula III wherein R 2 and R 3 have the meanings given above, with a lower-alkyl magnesium halide to obtain the compound of Formula I wherein R 4 is hydrogen, or reducing the compound of Formula I obtained with hydrogn in the presence of a catalyst to obtain the corresponding compound of Formula II, if desired, reacting the compound obtained wherein R4 is hydrogen with a lower-alkylating agent to obtain the compound wherein R 4 is lower-alkyl, if desired, reacting the compound obtained wherein R 4 is hydrogen with a lower alkanoic anhydride to produce the compound wherein R 4 is lower alkanoyl, if desired, reacting the compound obtained wherein R 4 is hydrogen with a molar equivalent of phosgene and reacting the resulting chloroformate with ammonia, a lower alkylamine, or a di-lower-alkylamine to produce the compound wherein R 4 is, respectively, carbamyl, N-lower-alkyl-carbamyl, or N,N-di-lower-alkylcarbamyl, if desired, reacting the compound obtained wherein R 4 is hydrogen with phosphorus oxychloride and reacting the resulting dichlorophosphinate with aqueous sodium or potassium carbonate to produce the compound wherein R 4 is phosphonyl, and, if desired, obtaining an acid-addition salt or quaternary ammonium salt of a basic compound obtained. (The term " lower " indicates radicals containing up to six carbon atoms.) Heterocyclic ketones of Formula III above are prepared by reaction of a compound of general Formula IV and a resorcinol of Formula V Substituted resorcinols of general Formula V above are prepared by dehydration of a 3,5-dilower-alkoxyphenyl alkyl (or cycloalkyl-loweralkyl) carbinol, reduction of the resulting 3,5-dilower-alkoxyphenyl-alkene (or di-lower-alkoxyphenyl-cycloalkyl.lower-alkene), and hydriodic acid cleavage of the ether groups to the corresponding 5-alkyl-(or 5.cycloalkyl-lower-alkyl-)- resorcinol. The starting carbinols in turn are prepared by reaction of an appropriate Grignard reagent with a 3,5-di-lower-alkoxybenzoic acid ester, amide, or 3<SP>1</SP>,5<SP>1</SP>-di-loweralkoxyalkanophenone (or 31, 5<SP>1</SP>-di-lower-alkoxy. cycloalkyl -lower-alkanophenone). Pharmaceutical compositions in conventional forms for oral or parenteral administration and having CNS depressant activity comprise an above novel compound and a carrier therefor.
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priorityDate 1965-09-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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Total number of triples: 39.