C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/356.1, 260/2
C07D 311/22 (2006.01) C07D 213/63 (2006.01) C07D 311/30 (2006.01)
Patent
CA 1061353
ABSTRACT OF THE DISCLOSURE This invention relates to new 5:6-benzo-.gamma.-pyrone derivatives of the general formula: Image (I) wherein: n is zero or 1; n1 is zero or 1; R may be: (a) cyano, carboxy or the Image radical; (b) -COR9 wherein R9 may be -NHOH or a Image 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 Image or the group Image , 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, Image wherein R10 and R11 are as hereabove defined, or R14 may be one of the radicals: Image , Image , Image , or Image ; 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, Image , 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 Image , 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, Image , wherein n3 is 2 or 3; and wherein the radical Image 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.
216961
Corno Maria L.
Doria Gianfederico
Giraldi Piernicola
Lauria Francesco
Sberze Piero
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