IE38544B1 - Benzo-or naphtho dipyran-di(n-tetrazolyl)-carboxamide derivatives methods for their production and compositions containing them - Google Patents

Abstract

1449810 Benzo- or naphtho-dipyran-dicarboxamide derivatives FISONS Ltd 16 Nov 1973 [5 Dec 1972 17 Aug 1973 (2)] 55997/72 39046/73 and 39047/73 Heading C2C [Also in Division A5] Novel compounds I and their salts in which two chains of Formula XX (in which each pair of R 9 and R 10 may be different and each R 9 and R 10 are selected from hydrogen, C 1-6 alkyl C 2-6 alkenyl, phenyl, phenyl C 1-6 alkyl, C 2-6 alkanoyl or C 2-6 alkoxycarbonyl) are attached to two pairs of ortho positions on a benzene or naphthalene nucleus which may be further substituted are prepared by (1) replacing a group R 12 with hydrogen (by using a hydrogen halide, catalytic hydrogenation, sodium in liquid ammonia, basic conditions or reactive diamination) in a compound in which two chains of Formula XXd are attached respectively to two pairs of ortho positions on a benzene or naphthalene nucleus which may be further substituted or removing both groups R 12 from a corresponding compound in which R 10 = R 12 to form a compound I (R 10 = H) (2) cyclizing a compound in which two chains of Formula XXe are attached to two pairs of ortho positions of an optionally further substituted benzene or naphthalene nucleus (3) reacting a compound in which two chains are attached to two pairs of ortho positions of an optionally further substituted benzene or naphthelene nucleus or an acid halide, ester or mixed anhydride thereof with a compound of Formula IV to form a compound I (R 9 =H when R 10 =H) (4) cyclizing a compound in which two pairs of groups -OH and (in which Y is -OH or NL 1 L 2 in which L 1 and L 2 are hydrogen phenyl or C 1-6 alkyl or together form a saturated or unsaturated 4 or 5 membered alkylene chain) are attached to two pairs of ortho positions on an optionally further substituted benzene or naphthalene nucleus or (5) selectively dehydrogenating a compound in which two chains of Formula XXf are attached to two pairs of ortho positions on an optionally further substituted benzene or naphthalene nucleus and, if desired, converting a compound I to a salt thereof compounds I prepared are those of Formulµ In, Io and Ip in which R 9 is hydrogen or methyl, R 10 is hydrogen, methyl, allyl carbethoxy, acetyl or benzyl and Pa and Qa are selected from hydrogen, C 1-5 alkyl, allyl, hydroxyl, chlorine, bromine, methoxy, ethoxy, allyloxy benzyloxy, nitro and ethoxymethyl, salts of a compound In (in which Qa, R 9 and R 10 are hydrogen and Pa is methoxy) with lithium, sodium, potassium, calcium, diethanolamine, tri-ethanolamine, tris-hydroxy methyl-methylamine, morpholine and N-methyl glucamine are also prepared. Compounds I inhibit antigen-antibody reactions. [GB1449810A]