Benzopyran derivatives
AssigneeAlkaloida Vegyeszeti Gyar
InventorsTibor Eszenyi, Peter Sebok, Laszlo Frank, Gyula Papp, Tibor Timar, Tamas Bartik
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Abstract
The invention relates to benzopyran compounds of formula (I) possessing pharmacological activity, as well as to pharmaceutical compositions containing the compounds of formula (I) and processes for the preparation thereof. ##STR1##
Claims17
A compound of the Formula (I) ##STR13## wherein R.sub.1 is C.sub.1 to C.sub.6 alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, aralkoxy, hydroxy, nitro, cyano, formyl, C.sub.1 to C.sub.6 acyl, cyano-C.sub.1 -C.sub.6 alkyl or halo;
- R.sub.2 is C.sub.1 to C.sub.6 alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, aralkoxy or hydroxy;
- or
- R.sub.1 and R.sub.2 together are alkylenedioxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.6 alkyl.
A compound of the Formula ##STR14## wherein R.sub.1 is nitro, cyano or cyano-C.sub.1 -C.sub.6 alkyl;
- R.sub.2 is C.sub.1 to C.sub.4 alkoxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.4 alkyl.
A process for the preparation of a compound of the Formula (I) ##STR15## wherein R.sub.1 is C.sub.1 to C.sub.6 alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, aralkoxy, hydroxy, nitro, cyano, formyl, C.sub.1 to C.sub.6 acyl, cyano-C.sub.1 -C.sub.6 alkyl or halo;
- R.sub.2 is C.sub.1 to C.sub.6 alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, aralkoxy or hydroxy;
- or
- R.sub.1 and R.sub.2 together are alkylenedioxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.6 alkyl, which comprises the steps of:
- (a) reducing a compound of the Formula (XVIII) ##STR16## with a metal hydride to yield a compound of the Formula (XIX) ##STR17## (b) dehydrating the compound of the Formula (XIX) by boiling said compound in a water immiscible solvent forming therewith an azeotropic mixture in the presence of a catalytically effective amount of p-toluene sulfonic acid to obtain a compound of the Formula (V) ##STR18## (c) converting the compound of the Formula (V) with N-bromo-succinimide to a compound of the Formula (VII) ##STR19## and (d) reacting the compound of the Formula (VII) with 2-pyrrolidone in the presence of an alkali metal alcoholate to obtain the compound of the Formula (I).
A process for preparing a compound of the Formula (X) ##STR20## wherein R.sub.2 is C.sub.1 to C.sub.4 alkoxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.4 alkyl, which comprises the step of nitrating a compound of the Formula (IX) ##STR21## with copper(II)nitrate in a carboxylic anhydride.
A process for the preparation of a compound of the Formula (XII) ##STR22## wherein R.sub.2 is C.sub.1 to C.sub.4 alkoxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.4 alkyl, which comprises the steps of
- (a) reacting a compound of the Formula (IX) ##STR23## in a mixture of phosphorous trichloride oxide and dimethyl formamide to obtain a compound of the Formula (XI) ##STR24## (b) dissolving the compound of the Formula (XI) in a carboxylic acid;
- and (c) boiling the dissolved compound of the Formula (XI) in the carboxylic acid in the presence of hydroxylamine hydrochloride and an alkali metal formiate.
A process for preparing a compound of the Formula (XV) ##STR25## wherein R.sub.2 is C.sub.1 to C.sub.4 alkoxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.1 to C.sub.4 alkyl, which comprises the step of:
- (a) condensing a compound of the Formula (XI) ##STR26## with acetonitrile in the presence of an alkali metal alcoholate to obtain a compound of the Formula (XIII) ##STR27## (b) reacting the compound of the Formula (XIII) with a mineral acid to yield a compound of the Formula (XIV) ##STR28## and;
- (c) hydrogenating the compound of the Formula (XIV) in the presence of a catalyst under pressure.
A process for preparing a compound of the Formula (XVIII) ##STR29## wherein R.sub.1 is hydrogen;
- R.sub.2 is hydroxy;
- and
- R.sub.3 and R.sub.4 are each C.sub.2 to C.sub.6 alkyl, which comprises reacting the compound of the Formula (XVI) ##STR30## with a compound of the Formula (XVII) ##STR31## in which R.sub.3 and R.sub.4 are each C.sub.2 to C.sub.6 alkyl.
Dependencies are inferred from the claim text.