Process for the preparation of 9-hydrazono-...

C - Chemistry – Metallurgy – 07 – D

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260/242.01

C07D 471/04 (2006.01)

Patent

CA 1153371

ABSTRACT OF THE DISCLOSURE The invention provides a process for the preparation of a nitrogen bridgehead compound of the formula I Image wherein R1 is hydrogen, lower alkyl, styryl, or lower alkoxycarbonyl; R2 is hydrogen or lower alkyl; R3 is carboxy, lower alkoxycarbonyl, carbamoyl, cyano, formyl, or lower alkyl; R4 is hydrogen, lower alkyl, hydroxyethyl, carboxy-lower alkyl, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, benzyl, 2-, 3- or 4-pyridyl, or benzothiazol-2-yl, phenyl or naphthyl or phenyl or naphthyl substituted by at least one of hydroxy, halogen, lower alkyl, sulfo, carboxy, lower alkoxy, methylenedioxy, amino, nitro and tri- fluoromethyl; R5 is hydrogen, lower alkanoyl, benzoyl or nicotinoyl or the group -NR4R5 is piperidinyl, pyrrolidinyl or morpholinyl, or a pharmaceuti- cally acceptable salt, hydrate, stereoisomer, optically active isomer, geo- metric isomer or tautomer thereof, which comprises reacting a racemic or optically active compound of the formula II Image wherein X is halogen, with a compound of the formula III Image or an acid addition salt thereof, at room temperature for a period of from 2 to 3 hours under vigorous stirring to a period of 2 to 3 days, standing, and, if required, converting an obtained salt to the free compound of formula I or converting a compound of formula I into a pharmaceutically acceptable acid addition salt. The compounds possess interesting antialler- gic and antiasthmatic properties and can be used orally, intravenously or by inhaling.

351676

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