Patent CA-1061353-A (CA)
Title: 5:6-BENZO-.gamma.-PYRONE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
Inventor: DORIA GIANFEDERICO
IPC: A61K31/352
Filed: 1974-12-27
Granted: 1979-08-28
Abstract: ABSTRACT OF THE DISCLOSURE This invention relates to new 5:6-benzo-.gamma.-pyrone derivatives of the general formula:             (I) wherein: n is zero or 1; n1 is zero or 1; R may be: (a) cyano, carboxy or the       radical; (b) -COR9 wherein R9 may be -NHOH or a   radical, wherein each of R10 and R11 may be hydrogen or C1-C6 alkyl, or, when R10 is hydrogen, R11 may also be the radical   or the group  ,  wherein R12 is hydrogen or C1-C6 alkyl or R10 and R11, taken together with the nitrogen atom, may be a N-pyrrolidinyl, piperidino or morpholino radical; (c) COOR13 wherein R13 is a C1-C12 alkyl or alkenyl group, which may be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, carboxy, hydroxy, -OR14 and -OCOR14 wherein R14 may be C1-C6 alkyl, substituted or unsubstituted phenyl,   wherein R10 and R11 are as hereabove defined, or R14 may be one of the radicals:       ,  ,  , or   ; wherein R13 is as hereabove defined;     each of R1 and R2' being the same or different, may be hydrogen or methyl; each of R3 and R4, being the same or different, may be hydrogen or C1-C6 alkyl; each of R5, R6, R7 and R8, being the same or different, may be: a')  hydrogen, halogen, hydroxy, nitro,  , wherein R10 and R11 are as defined above; b')  a radical -(O)m-R13, wherein m is zero or 1, and R13 is as hereabove define; c')  a radical -O-CO-R15,wherein R15 may have the same meanings above-mentioned for R13 or R15 may be a group  , wherein R10 and R11 are as hereabove defined; d')  a radical -S-R13, wherein R13 is as hereabove defined; or R7 and R8, when placed on adjacent carbon atoms, may represent, taken together, a methylenedioxy, ethylenedioxy or propylenedioxy group; X is phenyl or a pentatomic or hexatomic heteromonocyclic radical containing at least one double bond and one or two heteratoms selected from the group consisting of nitrogen, sulphur and oxygen; and wherein, when X is a nitrogen containing radical, a nitrogen atom may be bound to an oxygen atom to give the N-oxide; W may be ?= O,  , wherein n3 is 2 or 3; and wherein the radical   may be in the 6- or 7- position of the benzopyrone ring; and a pharmaceutically acceptable salt thereof; with the exclusion of the compounds wherein - when at the same time X is phenyl, W is-CO-, n and n1 are zero, R5, R6, R7 are hydrogen and R, in the 6--position, is carboxy, - R8 is hydrogen, or R8, in the 3' or 4'-position of the phenyl, is hydroxy, methoxy, chlorine, bromine, iodine, and with the further exclusion of the following compounds:     - 6-carboxy-3',4'-methylenedioxy-flavone;          - 6-carboxy-7-hydroxy-flavone;          - 6-carboxy-5-othoxy-4'-methoxy-flavone;          - 7-carboxy-flavone, - 6-(7,4'-dimethoxy)-flavonyl-acetic acid.  It also relates to the preparation of these compounds according to known methods.  The compounds of formula (I) together with their pharmaceutically acceptable salts possess anti-allergic activity on oral administration, which renders them useful in the prevention and treatment of bronchial asthma, allergic rhinitis, hay fever, urticaria and dermatosis.